2,6-Difluorobenzaldehyde → (R)-5-(1-(1-(2-fluoro-6-methylbenzyl)piperidin-3-yl)-1H-1,2,3-triazol-4-yl)-3-(pyridin-4-yl)-1H-indazole

HRID 1465695Notes

Reaction equation

HRID 1465695 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([N:7]2[CH:11]=[C:10]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][N:16]=[C:15]4[C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[N:9]=[N:8]2)[CH2:2]1.F[C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:29]=1[CH:30]=O.[C:37](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[F:36][C:32]1[CH:33]=[CH:34][CH:35]=[C:28]([CH3:37])[C:29]=1[CH2:30][N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([N:7]2[CH:11]=[C:10]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][N:16]=[C:15]4[C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[N:9]=[N:8]2)[CH2:2]1

Participants

5

Reactant 3

HCID 1362842,6-DifluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86695576(R)-5-(1-(piperidin-3-yl)-1H-1,2,3-triazol-4-yl)-3-(pyridin-4-yl)-1H-indazole

Product 1

HCID 86695577(R)-5-(1-(1-(2-fluoro-6-methylbenzyl)piperidin-3-yl)-1H-1,2,3-triazol-4-yl)-3-(pyridin-4-yl)-1H-indazoleYield 51.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-5-(1-(piperidin-3-yl)-1H-1,2,3-triazol-4-yl)-3-(pyridin-4-yl)-1H-indazole (0.05 g, 0.14 mmol) was dissolved in MeOH (3 mL) at 0° C., added 2,6-difluorobenzaldehyde (0.2 g, 1.4 mmol) and then sodium triacetoxyborohydride (0.0761 g, 0.37 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 3 h. Evaporated the solvent, subjected to Preparative Thin Layer chromatography to give (R)-5-(1-(1-(2-fluoro-6-methylbenzyl)piperidin-3-yl)-1H-1,2,3-triazol-4-yl)-3-(pyridin-4-yl)-1H-indazole (0.034 g).

Workup

  1. customEvaporated the solvent

Sources & evidence

ORD record
ord-4b543b40a5b24d5cb41654ab20aa1ea4
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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