Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH2:1]([O:3][P:4]([CH2:9][O:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14]Cl)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[Cl:16][C:17]1[N:25]=[C:24]([NH2:26])[N:23]=[C:22]2[C:18]=1[NH:19][CH:20]=[N:21]2.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:6]([O:5][P:4]([CH2:9][O:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14][N:21]1[CH:20]=[N:19][C:18]2[C:22]1=[N:23][C:24]([NH2:26])=[N:25][C:17]=2[Cl:16])([O:3][CH2:1][CH3:2])=[O:8])[CH3:7]
Reactant: CCOP(=O)(COC/C=C\CCl)OCC
Reactant: Nc1nc(Cl)c2[nH]cnc2n1
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: CN(C)C=O
Product: CCOP(=O)(COC/C=C\Cn1cnc2c(Cl)nc(N)nc21)OCC
Temperature: 20 °C
Reaction time: 48 h
Yield: 54.5 %

Procedure:
A mixture of Z-(4-chloro-2-butenyloxy)methyl phosphonic acid diethylester (1.05 g, 4 mmol), 6-chloro-2-aminopurine (1 g, 6 mmol) and potassium carbonate (0.92 g, 6 mmol) in anhydrous dimethylformamide (10 ml) is stirred 2 days at 20° C. The reaction mixture is concentrated in vacuo and the residue is purified by flash chromatography on silica gel to give the title product (0.85 g, 55%).
Reaction SMILES: [Cl:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=4)[N:15]=[C:14]3[CH2:25][O:26][CH2:27][CH3:28])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1C=CC(S(O[CH2:48][C@@H:49]2[O:51][CH2:50]2)(=O)=O)=CC=1.C1(O)C=CC=CC=1>CN(C=O)C>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:48][C@H:49]5[CH2:50][O:51]5)=[CH:20][CH:19]=4)[N:15]=[C:14]3[CH2:25][O:26][CH2:27][CH3:28])=[CH:11][CH:12]=2)=[CH:4][CH:3]=1
Reactant: Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1
Reactant: CCOCc1nc(-c2ccc(O)cc2)cn1-c1ccc(Oc2ccc(Cl)cc2)cc1
Agent: O=C([O-])[O-]
Agent: [Cs+]
Solvent: Oc1ccccc1
Solvent: CN(C)C=O
Product: CCOCc1nc(-c2ccc(OC[C@H]3CO3)cc2)cn1-c1ccc(Oc2ccc(Cl)cc2)cc1

Procedure:
A mixture of 4-{1-[4-(4-chloro-phenoxy)-phenyl]-2-ethoxymethyl-1H-imidazol-4-yl}-phenol (0.21 g, 0.5 mmol, 1.0 eq.) and Cs2CO3 (0.49 g, 1.5 mmol, 3.0 eq.) in DMF (2 mL) was stirred and preheated to 80° C. The reaction mixture was then treated with a solution of (2R)-(−)-glycidyl tosylate (0.17 g, 0.75 mmol, 1.5 eq.) in 1 mL of DMF dropwise, and further stirred at 80° C. for ˜30 min following completion of the addition. Analysis of the reaction by TLC and LC/MS showed that the starting phenol had been consumed and the desired alkylated-phenol was the major product. The reaction was then cooled and diluted with EtOAc and washed with brine. The organic phase was dried with Na2SO4 and evaporated in vacuo. The crude alkylated-phenol was then purified by flash column chromatography over silica gel (EtOAc/hexanes ˜1:3).
Reaction SMILES: [CH:1]1([N:4]([CH3:26])[C:5]2[N:25]=[C:8]3[CH:9]=[C:10]([NH:13][C:14]([C:16]4[N:20]([CH3:21])[N:19]=[CH:18][C:17]=4[C:22]([OH:24])=O)=[O:15])[CH:11]=[CH:12][N:7]3[N:6]=2)[CH2:3][CH2:2]1.[NH:27]1[CH2:30][CH2:29][CH2:28]1>>[CH:1]1([N:4]([CH3:26])[C:5]2[N:25]=[C:8]3[CH:9]=[C:10]([NH:13][C:14]([C:16]4[N:20]([CH3:21])[N:19]=[CH:18][C:17]=4[C:22]([N:27]4[CH2:30][CH2:29][CH2:28]4)=[O:24])=[O:15])[CH:11]=[CH:12][N:7]3[N:6]=2)[CH2:3][CH2:2]1
Reactant: CN(c1nc2cc(NC(=O)c3c(C(=O)O)cnn3C)ccn2n1)C1CC1
Reactant: C1CNC1
Product: CN(c1nc2cc(NC(=O)c3c(C(=O)N4CCC4)cnn3C)ccn2n1)C1CC1
Yield: 83.7 %

Procedure:
The product was prepared in the same manner as described in example 70f using 5-(2-(cyclopropyl(methyl)amino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (70 mg, 197 μmol) and azetidine (52.9 μl, 788 μmol) as starting materials. The reaction affords 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(cyclopropyl-methyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide (65 mg, 83.7%) as off-white solid. mp: 229.6, MS: m/z=395.0 (M+H+).
Reaction SMILES: C([O:3][C:4]([C:6]1[CH:7]=[C:8](B(O)O)[CH:9]=[CH:10][CH:11]=1)=[O:5])C.Br[C:16]1[C:17]([Cl:36])=[C:18]([C:32]([Cl:35])=[CH:33][CH:34]=1)[CH2:19][CH:20]1[CH2:24][CH2:23][N:22]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:21]1=[O:31].COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[Cl:35][C:32]1[C:18]([CH2:19][CH:20]2[CH2:24][CH2:23][N:22]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:21]2=[O:31])=[C:17]([Cl:36])[CH:16]=[CH:34][C:33]=1[C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:4]([OH:3])=[O:5])[CH:7]=1
Reactant: O=C1C(Cc2c(Cl)ccc(Br)c2Cl)CCN1C1CCCCC1
Reactant: CCOC(=O)c1cccc(B(O)O)c1
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: O=C([O-])[O-]
Agent: [Na+]
Solvent: ClCCl
Solvent: COCCOC
Product: O=C(O)c1cccc(-c2ccc(Cl)c(CC3CCN(C4CCCCC4)C3=O)c2Cl)c1
Temperature: 25 °C
Reaction time: 1 h
Yield: 94.1 %

Procedure:
Place 3-(ethoxycarbonyl)phenylboronic acid (670 mg, 3.46 mmol), 3-(3-bromo-2,6-dichlorobenzyl)-1-cyclohexylpyrrolidin-2-one (Example 50) (700 mg, 1.73 mmol), and Pd(PPh3)4 (173 mg, 0.173 mmol) into a flask and purge with nitrogen. Add DME (50 mL) and 2M sodium carbonate (5 mL) and heat to 75° C. for 24 hr. Cool reaction, add DCM and wash with saturated sodium bicarbonate. Dry, filter, and concentrate organic layer. Purify by silica gel (30-45% EtOAc in Hex). Dissolve ester in ethanol (3 mL) and water (1 mL) and add KOH (291 mg, 5.18 mmol. Stir for 1 hour at room temperature. Strip off solvent and add water. Bring to a pH of 2 with 1M HCl. Filter precipitate to give 727 mg (94%) of title compound as a white solid. Mass spectrum (apci) m/z=446.2 (M+H).