2-Fluoro-6-methoxybenzaldehyde → HCID 86681281, compound

HRID 1467335Notes

Reaction equation

HRID 1467335 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][C:16]1[CH:21]=[C:20]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:31]([NH:33][C@H:34]4[CH2:39][NH:38][C@H:37]([C:40]([O:42][CH3:43])=[O:41])[CH2:36][CH2:35]4)=[O:32])[CH:29]=3)[NH:24][N:23]=2)[CH:19]=[CH:18][N:17]=1.[F:44][C:45]1[CH:52]=[CH:51][CH:50]=[C:49]([O:53][CH3:54])[C:46]=1[CH:47]=O>CO>[F:44][C:45]1[CH:52]=[CH:51][CH:50]=[C:49]([O:53][CH3:54])[C:46]=1[CH2:47][N:38]1[CH2:39][C@H:34]([NH:33][C:31]([C:28]2[CH:29]=[C:30]3[C:25](=[CH:26][CH:27]=2)[NH:24][N:23]=[C:22]3[C:20]2[CH:19]=[CH:18][N:17]=[C:16]([CH3:15])[CH:21]=2)=[O:32])[CH2:35][CH2:36][C@H:37]1[C:40]([O:42][CH3:43])=[O:41]

Participants

5

Reactant 3

HCID 27373572-Fluoro-6-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67997234HCID 67997234, compound

Product 1

HCID 86681281HCID 86681281, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

SODIUM TRIACETOXYBOROHYDRIDE (6.46 g, 30.5 mmol) was added to a stirred mixture of (2S,5R)-methyl 5-(3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamido)-piperidine-2-carboxylate (2 g, 5 mmol) and 2-Fluoro-6-Methoxy-Benzaldehyde (4.70 g, 30.5 mmol) in MeOH (100 ml) and the mixture was stirred at room temperature for overnight. The reaction LCMS gave M+H at 532. The reaction was rotovap to dryness and the residue was purified by column chromatography on silica gel Biotage 40M, eluting with 5% MeOH/NH3(2M)CH2Cl2 to give desired product as a brown solid (2 g, 3.76 mmol, 74.0% yield).

Workup

  1. customThe reaction LCMS
  2. customgave M+H at 532
  3. customthe residue was purified by column chromatography on silica gel Biotage 40M
  4. washeluting with 5% MeOH/NH3(2M)CH2Cl2

Sources & evidence

ORD record
ord-e72e05a910f2409cb2eccd18008de3e8
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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