Water → {5-[Hydroxy-(5-triisopropylsilanyloxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-pyridin-2-yl}-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester

HRID 1256757Notes

Reaction equation

HRID 1256757 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][N:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH:28]([Si:31]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[O:32][C:33]1[CH:34]=[C:35]2[CH:41]=[CH:40][NH:39][C:36]2=[N:37][CH:38]=1)([CH3:30])[CH3:29].[OH-].[K+].O>CO>[C:1]([O:5][C:6](=[O:27])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]([OH:26])[C:41]2[C:35]3[C:36](=[N:37][CH:38]=[C:33]([O:32][Si:31]([CH:42]([CH3:44])[CH3:43])([CH:45]([CH3:47])[CH3:46])[CH:28]([CH3:29])[CH3:30])[CH:34]=3)[NH:39][CH:40]=2)=[CH:21][N:20]=1)[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 59593275(5-Formyl-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl esterHCID 595933245-Triisopropylsilanyloxy-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59593260{5-[Hydroxy-(5-triisopropylsilanyloxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-pyridin-2-yl}-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (5-Formyl-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester (19, 41 mg, 0.11 mmol, prepared as described in Example 30), 5-triisopropylsilanyloxy-1H-pyrrolo[2,3-b]pyridine (83, 34 mg, 0.12 mmol) and potassium hydroxide (9.8 mg, 0.17 mmol) in methanol (10 mL) was stirred at room temperature overnight. The reaction mixture was poured into water, extracted with ethyl acetate, washed with brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a viscous liquid (84, 0.05 g, 70%). MS (ESI) [M+H+]+=671.38.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent
  5. customthe residue was purified by silica gel column chromatography
  6. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-a9c08b9af4b54262ab40f931a4ec300f
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

Loading…