Water → [3-benzyloxy-2-cyclopropylmethoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

HRID 253451Notes

Reaction equation

HRID 253451 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH2:11]([O:18][C:19]1[C:20]([O:27][CH2:28][CH:29]2[CH2:31][CH2:30]2)=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[O:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[K+].O>CO>[CH2:11]([O:18][C:19]1[C:20]([O:27][CH2:28][CH:29]2[CH2:31][CH2:30]2)=[C:21]([CH:22]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[NH:8][CH:9]=2)[OH:23])[CH:24]=[CH:25][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 598038783-Benzyloxy-2-cyclopropylmethoxy-benzaldehyde

Product 1

HCID 59803823[3-benzyloxy-2-cyclopropylmethoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanolYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-chloro-1H-Pyrrolo[2,3-b]pyridine (4, 0.68 g, 4.46 mmol, prepared as described in Example 4), 3-benzyloxy-2-cyclopropylmethoxy-benzaldehyde (130, 1.2 g, 4.25 mmol), and potassium hydroxide (0.68 g, 11 mmol) in methanol (50 mL) was stirred at room temperature for 4 days. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was collected, 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 compound as a white solid (131, 0.99 g, 54%). MS (ESI) [M+H+]+=435.21.

Workup

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

Sources & evidence

ORD record
ord-7a2d3b950af14c51b5e6c1029f08d804
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

Loading…