Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH:1]1([NH:4][C:5]([C@@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12](=[O:15])[CH2:13]Br)=[O:6])[CH2:3][CH2:2]1.[CH2:16]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27](=[O:52])[C@@H:28]([NH:38][C:39]([C:41]2[CH:50]=[C:49]([OH:51])[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH:42]=2)=[O:40])[CH2:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[CH2:23][CH2:22]1)=[O:20])[CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH2:16]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27](=[O:52])[C@@H:28]([NH:38][C:39]([C:41]2[CH:50]=[C:49]([O:51][CH2:13][C:12]([N:8]3[CH2:9][CH2:10][CH2:11][C@H:7]3[C:5](=[O:6])[NH:4][CH:1]3[CH2:3][CH2:2]3)=[O:15])[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH:42]=2)=[O:40])[CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH2:23][CH2:22]1)=[O:20])[CH3:17]
Reactant: O=C(NC1CC1)[C@@H]1CCCN1C(=O)CBr
Reactant: CCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)c2cc(O)c3ccccc3c2)CC1
Agent: O=C([O-])[O-]
Agent: [Cs+]
Solvent: O
Solvent: CN(C)C=O
Product: CCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)O)NC(=O)c2cc(OCC(=O)N3CCC[C@H]3C(=O)NC3CC3)c3ccccc3c2)CC1
Temperature: 80 °C

Procedure:
To a solution of 100 mg of (S)-1-(2-Bromo-acetyl)-pyrrolidine-2-carboxylic acid cyclopropylamide and 93 mg of 4-{(S)-4-tert-Butoxycarbonyl-2-[(4-hydroxy-naphthalene-2-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester in 2 ml of DMF, 118 mg of cesium carbonate was added and the reaction mixture was heated to 80° C. for 5 h. Then, the reaction mixture was diluted with water and filtered through a chem Elut® cartridge by eluting with ethyl acetate. The solvents were removed under reduced pressure and the residue was dissolved in 1 ml of DCM and 0.2 ml of TFA. After 16 h at RT 10 ml of toluene was added and the solvents were removed under reduced pressure. The residue was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a white solid. Yield: 40 mg MS (ES+): m/e=652.
Reaction SMILES: Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[N:3]=1.[C:15]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:16]=1.C(C([Sn])=C(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[N+:12]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([CH:15]=[CH2:16])=[N:3]2)([O-:14])=[O:13]
Reactant: O=[N+]([O-])c1cccc2nc(Cl)ccc12
Reactant: c1ccc(P(c2ccccc2)c2ccccc2)cc1
Agent: CCCCC([Sn])=C(CCCC)CCCC
Solvent: Cc1ccccc1
Product: C=Cc1ccc2c([N+](=O)[O-])cccc2n1

Procedure:
5.06 g (24.5 mmol) of 2-chloro-5-nitroquinoline, 1.26 g (4.9 mmol) of triphenylphosphine and 8.0 g (25.2 mmol) of tri-n-butylvinyltin are dissolved in 60 ml of toluene. After adding 2.75 g (2.5 mmol) of tris(dibenzylidenacetone)dipalladium, the reaction mixture is allowed to reflux for 20 hours. Then, it is filtered on Celite and washed with ethyl acetate. The filtrate is mixed with saturated ammonium chloride solution. It is extracted with ethyl acetate, and the combined organic phases are dried on sodium sulfate. After the solvent is removed in a vacuum and after subsequent chromatography on silica gel with hexane-ethyl acetate (5-20%), 3.05 g (62% of theory) of the product is obtained.
Reaction SMILES: [C:1]1([C:7]2[CH2:11][CH:10]([CH2:12][CH2:13][CH2:14][CH:15]=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([CH3:29])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:1]1([C:7]2[CH2:11][CH:10]([CH2:12][CH2:13][CH2:14][CH2:15][N:26]3[CH2:27][CH2:28][N:23]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[CH3:29])[CH2:24][CH2:25]3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
Reactant: O=CCCCC1CC(c2ccccc2)=NO1
Reactant: Cc1ccccc1N1CCNCC1
Agent: CC(=O)O[BH-](OC(C)=O)OC(C)=O
Agent: [Na+]
Solvent: ClCCl
Product: Cc1ccccc1N1CCN(CCCCC2CC(c3ccccc3)=NO2)CC1
Yield: 62.1 %

Procedure:
4-(3-Phenyl-4,5-dihydroisoxazol-5-yl)butanal (27.1 mg, 0.124 mmol), 1-(o-tolyl) piperazine (20.0 mg, 0.113 mmol), molecular sieve (5 beads) and NaBH(OAc)3 (72.1 mg, 0.340 mmol) were reacted in 3 mL of methylene chloride for about 12 hr. With the following processes the same as in Example 1, 26.5 mg (67.3%) of the target compound was obtained.