Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: Br[C:2]1[C:3]([CH:9]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:8])[S:5][C:6]=1[Cl:7].CC1(C)C(C)(C)OB([C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[O:34][CH2:33][CH2:32][CH2:31]3)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:16]([O:15][CH:9]([C:3]1[C:2]([C:28]2[CH:37]=[CH:36][C:35]3[O:34][CH2:33][CH2:32][CH2:31][C:30]=3[CH:29]=2)=[C:6]([Cl:7])[S:5][C:4]=1[CH3:8])[C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH3:19])([CH3:18])[CH3:17]
Reactant: CC1(C)OB(c2ccc3c(c2)CCCO3)OC1(C)C
Reactant: CCOC(=O)C(OC(C)(C)C)c1c(C)sc(Cl)c1Br
Agent: c1ccc([P]([Pd][P](c2ccccc2)(c2ccccc2)c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: O=C([O-])[O-]
Agent: [Na+]
Solvent: O
Solvent: C1COCCO1
Product: CCOC(=O)C(OC(C)(C)C)c1c(C)sc(Cl)c1-c1ccc2c(c1)CCCO2
Temperature: 85 °C
Reaction time: 8 h
Yield: 54.1 %

Procedure:
Under argon atmosphere, ethyl 2-(4-bromo-5-chloro-2-methylthiophen-3-yl)-2-(tert-butoxy)acetate (44d) (500 mg, 1.35 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (351.8 mg, 1.35 mmol), sodium carbonate (429 mg, 4.05 mmol) were dissolved in dioxane (28 mL) and water (4 mL). The solution was degassed under argon for 10 minutes and bis(triphenylphosphine)palladium (II) dichloride (142 mg, 0.20 mmol) was added. The reaction was heated and shaken at 85° C. for 8 hours. After cooling at room temperature, the mixture was filtered through celite, rinsed with methanol. The filtrate was concentrated in vacuo and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 97/3) to give the desired product (44e) (308 mg, 0.73 mmol, 54%).
Reaction SMILES: CO[N:3]=[C:4]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH:5]([NH2:12])[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[Li]>C(OCC)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([CH:4]([NH2:3])[CH:5]([NH2:12])[CH2:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:18][CH:17]=1
Reactant: CON=C(c1ccc(Cl)cc1)C(N)CC1CCCC1
Agent: [Li]
Solvent: CCOCC
Product: NC(CC1CCCC1)C(N)c1ccc(Cl)cc1
Temperature: 0 °C
Reaction time: 3 h

Procedure:
A solution of 2-amino-1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime (420 mg, 1.567 mmol) in diethyl ether (3 mL) was added dropwise to a slurry mixture of lithium aluminumhydride (307 mg, 7.835 mmol) in diethyl ether (30 mL) cooled to 0° C. At the end of addition, the icebath was removed and the reaction was stirred at room temperature for 3 h. The reaction mixture was cooled to 0° C. and aqueous solution of sodium chloride was added to quench the excess lithium aluminumhydride. Sodium hydroxide solution was added and the biphasic mixture was stirred for 1 h. The product was extracted with diethyl ether (3×30 mL). The ethereal extracts were washed with brine and dried over anhydrous sodium sulfate. Evaporation of the solvent gave 1-(4-chloro-phenyl)-3-cyclopentyl-propane-1,2-diamine as yellow oil (362.7 mg, 96%, 4.3:1.0 ratio of cis:trans). The crude product was used without further purification.
Reaction SMILES: C(O)CCO.C(OC)(=O)C1C=CC(C(OC)=O)=CC=1.[CH:20]1[C:29]2[C:24](=[CH:25][C:26]([C:30]([O:32]C)=[O:31])=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[C:34]([O:36]C)=[O:35].O=[Sb]O[Sb]=O>C(O)CCC.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].O.O.O.O.C([O-])(=O)C.C([O-])(=O)C.[Mn+2].O.O.O.O.C([O-])(=O)C.C([O-])(=O)C.[Co+2]>[CH:20]1[C:29]2[C:24](=[CH:25][C:26]([C:30]([OH:32])=[O:31])=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[C:34]([OH:36])=[O:35]
Reactant: COC(=O)c1ccc2cc(C(=O)OC)ccc2c1
Agent: [Co+2]
Agent: [Mn+2]
Agent: [Ti+4]
Solvent: O
Solvent: OCCCO
Solvent: CCCCO
Product: O=C(O)c1ccc2cc(C(=O)O)ccc2c1
Temperature: 210 °C

Procedure:
In this example, a poly(trimethylene terephthalate) copolyester containing 9 mole % 2,6-naphthalenedicarboxylic acid was prepared. 79.8 grams (1.05 moles) of 1,3-propanediol, 124.2 grams (0.64 moles) of dimethyl terephthalate, 14.6 grams (0.06 moles) of dimethyl 2,6-naphthalenedicarboxylate, 0.25 ml of butanol solution containing 30 grams titanium tetraisopropoxide in 500 ml of n-butanol, 0.0354 grams manganese diacetate tetrahydrate, 0.0488 grams cobalt diacetate tetrahydrate, and 0.0397 grams antimony trioxide were added to a 500 ml 3-necked round bottom flask equipped with a ground glass head, a stirrer, and a nitrogen inlet. The flask was immersed in a Belmont metal bath and heated for 2 hours at 200° C. and 1 hour at 210° C. After this time the theoretical amount of methanol was collected. 1.95 ml of a solution containing 173 grams ZONYL A in 185 ml butanol and 1192 ml of 1,3-propanediol were added and the temperature was increased to 280° C. The pressure in the flask was reduced from atmospheric to between about 0.1 to 0.5 mm of Hg for 90 minutes. Stirring was reduced as the viscosity increased until a stir rate of 25 RPM was obtained. The vacuum was discontinued and nitrogen was bled into the flask. The polymer was allowed to solidify by cooling to below Tg, removed from the flask and ground to pass a 3 mm screen. The inherent viscosity of the polymer in the melt phase was 0.62. The polymer had a Tm of 211° C. and a Tg value of 56° C. No Tcc was present under the scan conditions of 20° C./min. Compositional analysis (by NMR) showed that the copolyester contained 9 mole % 2,6 naphthalenedicarboxylic acid.
Reaction SMILES: FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[N:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)=[CH:9][CH:8]=1)(=O)=O.[C:26]([C:28]1[CH:29]=[C:30]([Sn](C)(C)C)[CH:31]=[N:32][CH:33]=1)#[N:27].C(N(CC)CC)C.[Cl-].[Li+]>C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.CN(C)C=O>[C:26]([C:28]1[CH:29]=[C:30]([C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][CH:13]=[C:14]3[N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:9][CH:8]=2)[CH:31]=[N:32][CH:33]=1)#[N:27]
Reactant: CN1CCN(c2cccc3ccc(OS(=O)(=O)C(F)(F)F)cc23)CC1
Reactant: C[Sn](C)(C)c1cncc(C#N)c1
Agent: Cc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1
Agent: [Cl-]
Agent: [Li+]
Solvent: CN(C)C=O
Solvent: CCN(CC)CC
Product: CN1CCN(c2cccc3ccc(-c4cncc(C#N)c4)cc23)CC1
Yield: 34 %

Procedure:
A mixture of 7-trifluoromethylsulfonyloxy-1-(4-methylpiperazin-1-yl)naphthalene (0.527 g, 1.53 mmol), bis(triphenylphosphine)palladium[II]chloride (0.537 g, 0.77 mmol), 5-cyano-3-trimethylstannylpyridine (0.0.450 g, 1.69 mmol, from preparation 7), triethylamine (1.02 mL, 7.34 mmol), lithium chloride (0.194 g, 4.59 mmol), 2,6-di-tert-butyl-4-methylphenol (approximately 0.01 g), and N,N-dimethylformamide (6 mL) was heated between 100° C. to 115° C. under nitrogen for 1.5 hours. The resulting mixture was concentrated via evaporation under reduced pressure, and the residue was column chromatographed using silica gel (approximately 25 g) and elution with 5% methanol in ethyl acetate to afford the title compound (0.170 g, 0.52 mmol, 34%) as a pale yellow foam: Rf =0.40 in 5% methanol in ethyl acetate; 1H (CD3OD) δ 9.08 (d, J=2.2 Hz, 1H), 8.82 (d, J=2.2 Hz, 1H), 8.43 (t, J=2.0 Hz, 1H), 8.36 (br s, 1H), 7.92 (d, J=8.5 Hz, 1H), 7.70 (dd, J=1.8 and 8.5 Hz, 1H), 7.57 (br d, J=8.2 Hz, 1H), 7.44 (t, J=7.8 Hz, 1H), 7.17 (d, J=7.3 Hz, 1H), 3.20-3.00 (br s, 4H), 2.85-2.65 (br s, 4H), 2.40 (s, 3H); LRMS (m/z, relative intensity) 328 (M+, 100); HRMS m/e calculated for C21H20N4 328.1690. Observed m/e 328.1715
Reaction SMILES: C[O:2][CH:3](OC)[CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11]>O1CCCC1>[O:11]=[C:6]1[CH2:7][CH2:8][CH2:9][CH2:10][N:5]1[CH2:4][CH:3]=[O:2]
Reactant: COC(CN1CCCCC1=O)OC
Solvent: C1CCOC1
Product: O=CCN1CCCCC1=O
Yield: 86.2 %

Procedure:
A mixture of 1-(2,2-dimethoxyethyl)-piperidin-2-one (1.06 g, 5.67 mmole) in 5% aqueous tetrahydrofuran (20 mL) was heated under reflux for 1 hour. The mixture was dried with anhydrous magnesium sulfate, filtered, and concentrated to give (2-oxo-piperidin-1-yl)-acetaldehyde (0.69 g) as a pale yellow oil.
Reaction SMILES: Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[Na].[CH3:20][CH:21]1[CH2:25][CH2:24][CH2:23][NH:22]1>C(#N)C>[OH:18][C@H:15]1[CH2:16][CH2:17][C@H:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:22]3[CH2:23][CH2:24][CH2:25][CH:21]3[CH3:20])=[CH:7][CH:8]=2)[CH2:13][CH2:14]1
Reactant: O[C@H]1CC[C@H](c2ccc(OCCCCl)cc2)CC1
Reactant: CC1CCCN1
Agent: [Na]
Solvent: CC#N
Product: CC1CCCN1CCCOc1ccc([C@H]2CC[C@H](O)CC2)cc1

Procedure:
A A mixture of trans-4-[4-(3-chloropropoxy)phenyl]cyclohexanol (403 mg), sodium hydrogenocarbonate (252 mg) potassium iodide (10 mg) and 2-methylpyrrolidine (153 mg) in acetonitrile (10 mL) is heated for 24 hours under reflux, then concentrated under reduced pressure. The residue is dissolved in ethyl acetate (25 mL). The organic phase is washed with water (5 mL), dried over magnesium sulfate, concentrated under reduced pressure and purified by chromatography over silica gel (eluent dichloromethane/methanol from 98/2 to 90/10). Fractions containing the expected product are pooled and concentrated under reduced pressure to give 120 mg of 1-{3-[trans-4-(4-hydroxycyclohexyl)phenoxy]propyl}-2-methylpyrrolidine as a white solid melting at 80° C.
Reaction SMILES: [BrH:1].Br.[C:3]1([CH2:9]N2C[C@H]3C[C@@H]2CN3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O.[Pd]>[BrH:1].[BrH:1].[CH3:9][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
Reactant: c1ccc(CN2C[C@H]3C[C@@H]2CN3)cc1
Agent: [Pd]
Agent: Br
Solvent: O
Product: CCCCCCC
Reaction time: 8 h
Yield: 180.8 %

Procedure:
A suspension of 76 g (0.217 moles) of (1R, 4R)-5-phenylmethyl-2,5-diazabicyclo-[2.2.1]-heptane, dihydrobromide (9) and 37 g of 10% Pd on C in 1.2 L of water was hydrogenated at atmospheric pressure at 40° C. The reaction was completed within 8 hours. The catalyst was filtered off and the filtrate was evaporated under reduced pressure. The residue was taken up with ethanol and the resulting precipitate was filtered to give 51.4 g (91%) of the titled compound. M.P.=285°. [α]D =-19.83 (c=1.2, 0.1N HCL).
Reaction SMILES: Cl.[NH2:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.C(N(CC)CC)C.[F:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33].N(CC)(CC)CC.Cl>C(Cl)Cl.C(O)C.O>[F:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([NH:2][C:3]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:5][C:4]=1[N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1)=[O:33]
Reactant: Nc1cc(C(F)(F)F)ccc1N1CCc2ccccc21
Reactant: O=C(Cl)c1ccccc1F
Agent: Cl
Solvent: ClCCl
Solvent: CCO
Solvent: O
Product: O=C(Nc1cc(C(F)(F)F)ccc1N1CCc2ccccc21)c1ccccc1F
Temperature: 25 °C
Reaction time: 8 h

Procedure:
To a stirred mixture, under N2, of 10.2 g of 1-(2-amino-4-trifluoromethylphenyl)indoline hydrochloride in 100 ml of dry methylene chloride is added 7.08 g of triethylamine. The mixture is cooled to 0°-5° C., and kept at that temperature while a solution of 5.71 g of o-fluorobenzoyl chloride in 50 ml of dry methylene chloride is added dropwise over 1 hour. After stirring at room temperature overnight, water is added to dissolve the precipitated (C2H5)3N.HCl salt, and the layers are separated. The organic phase is washed further with 3 N--HCl, 3 N--NaOH, with water and dried over sodium sulfate. The solvent is removed leaving an oil which is dissolved in 25 ml of ethanol and sets solid on cooling. The crystals are collected, washed with ethanol, and dried to afford 1-[2'-(2-fluorobenzoylamino)-4'-trifluoromethylphenyl]indoline, m.p. 127°-130° C.