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

HRID 1465688Notes

Reaction equation

HRID 1465688 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]2[N:8]=[N:9][N: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)[CH:11]=2)[CH2:2]1.[F:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:29]=1[CH:30]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[F:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:29]=1[CH2:30][N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]2[N:8]=[N:9][N: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:22]=[CH:23][N:24]=[CH:25][CH:26]=3)[CH:11]=2)[CH2:2]1

Participants

5

Reactant 3

HCID 1362842,6-DifluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86695572(R)-5-(4-(piperidin-3-yl)-1H-1,2,3-triazol-1-yl)-3-(pyridin-4-yl)-1H-indazole

Product 1

HCID 56968767(R)-5-(4-(1-(2,6-difluorobenzyl)piperidin-3-yl)-1H-1,2,3-triazol-1-yl)-3-(pyridin-4-yl)-1H-indazoleYield 26.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (R)-5-(4-(piperidin-3-yl)-1H-1,2,3-triazol-1-yl)-3-(pyridin-4-yl)-1H-indazole (0.075 g, 0.2 mmol) dissolved in MeOH (3 mL) at 0° C. was added 2,6-difluorobenzaldehyde (0.29 g, 2.1 mmol) and then sodium triacetoxyborohydride (0.11 g, 0.5 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-(4-(1-(2,6-difluorobenzyl)piperidin-3-yl)-1H-1,2,3-triazol-1-yl)-3-(pyridin-4-yl)-1H-indazole (0.025 g).

Workup

  1. customEvaporated the solvent

Sources & evidence

ORD record
ord-c778a6e8b83c4589ae482988e2421662
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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