Water → 2,4-difluoro-3-[hydroxy-(5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-phenol

HRID 250669Notes

Reaction equation

HRID 250669 reaction equation
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[CH:5]=[CH:4][C:3]=1[O:11]C(=O)OC(C)(C)C.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[CH:26]=[C:27]3[CH:33]=[CH:32][NH:31][C:28]3=[N:29][CH:30]=2)[CH:20]=1.[OH-].[K+].O>CO>[F:1][C:2]1[C:7]([CH:8]([OH:9])[C:33]2[C:27]3[C:28](=[N:29][CH:30]=[C:25]([C:21]4[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=4)[CH:26]=3)[NH:31][CH:32]=2)=[C:6]([F:10])[CH:5]=[CH:4][C:3]=1[OH:11]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 513585515-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridineHCID 58086191Carbonic acid tert-butyl ester 2,4-difluoro-3-formyl-phenyl ester

Product 1

HCID 580862122,4-difluoro-3-[hydroxy-(5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To carbonic acid tert-butyl ester 2,4-difluoro-3-formyl-phenyl ester (39, 0.405 g, 15.7 mmol) in methanol (36 mL), under an atmosphere of nitrogen, was added 5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine (89, 288.0 mg, 14.8 mmol, prepared as in Example 17, Scheme 32) and potassium hydroxide (145.0 mg, 25.9 mol). 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 concentrated. The desired compound was isolated by silica gel column chromatography eluting with 4% methanol in methylene chloride to give a colorless oil (P-0009, 0.23 g, 44.1%). MS (ESI) [M+H+]+=354.1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-62a7c56aa92748e289800f0b15d28d59
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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