Water → (3-dibenzylamino-2,6-difluoro-phenyl)-(5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

HRID 1964861Notes

Reaction equation

HRID 1964861 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:9]1[C:10]([F:18])=[C:11]([C:14]([F:17])=[CH:15][CH:16]=1)[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[CH:33]=[C:34]3[CH:40]=[CH:39][NH:38][C:35]3=[N:36][CH:37]=2)[CH:27]=1.[OH-].[K+].O>CO>[CH2:19]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[C:10]([F:18])=[C:11]([CH:12]([C:40]2[C:34]3[C:35](=[N:36][CH:37]=[C:32]([C:28]4[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=4)[CH:33]=3)[NH:38][CH:39]=2)[OH:13])[C:14]([F:17])=[CH:15][CH:16]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 513585515-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridineHCID 580878843-Dibenzylamino-2,6-difluoro-benzaldehyde

Product 1

HCID 58087074(3-dibenzylamino-2,6-difluoro-phenyl)-(5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3-dibenzylamino-2,6-difluoro-benzaldehyde (53, 0.76 g, 2.3 mmol) in methanol (50 mL) were added 5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine (89, 0.40 g, 2.1 mmol, prepared as described in Example 17) and potassium hydroxide (0.50 g, 8.9 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 5% methanol in methylene chloride to provide the compound (54, 0.60 g, 50%). MS(ESI) [M+H+]+=533.2.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 5% methanol in methylene chloride
  8. customto provide the compound (54, 0.60 g, 50%)

Sources & evidence

ORD record
ord-4ec2a0610cac4495a67d0e0de9a4dc6b
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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