2-Fluoro-6-methoxybenzaldehyde → HCID 67517547, compound

HRID 1465701Notes

Reaction equation

HRID 1465701 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=O.[NH:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]2[NH:22][N:21]=[C:20]([C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[NH:28][N:27]=[C:26]4[C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)[N:19]=2)[CH2:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH2:4][N:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]2[NH:22][N:21]=[C:20]([C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[NH:28][N:27]=[C:26]4[C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)[N:19]=2)[CH2:13]1

Participants

5

Reactant 3

HCID 27373572-Fluoro-6-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67518282HCID 67518282, compound

Product 1

HCID 67517547HCID 67517547, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Added 2-Fluoro-6-methoxy benzaldehyde (69 mg, 0.44 mmol) to a mixture of (R)-5-(5-(piperidin-3-yl)-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole (96 mg, 0.277 mmol) and sodium triacetoxy borohydride (176 mg, 0.833 mmol) in MeOH (8 ml) at room temperature. After stirred for 30 minutes, the solvent was evaporated. Diluted with EtOAc (150 ml), washed with H2O (50 ml), dried (Na2SO4) and concentrated. Crude product was purified on silica gel eluting with 5% v/v MeOH/CH2Cl2 to yield (R)-5-(5-(1-(2-fluoro-6-methoxybenzyl)piperidin-3-yl)-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole as a white solid (54 mg).

Workup

  1. customthe solvent was evaporated
  2. additionDiluted with EtOAc (150 ml)
  3. washwashed with H2O (50 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customCrude product was purified on silica gel eluting with 5% v/v MeOH/CH2Cl2

Sources & evidence

ORD record
ord-ceef6e827a6840d2981057598614ea1b
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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