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

HRID 1964973Notes

Reaction equation

HRID 1964973 reaction equation
C(=O)(O)O.[F:5][C:6]1[C:11]([CH:12]=[O:13])=[C:10]([F:14])[CH:9]=[CH:8][C:7]=1[O:15]C(=O)OC(C)(C)C.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[CH:30]=[C:31]3[CH:37]=[CH:36][NH:35][C:32]3=[N:33][CH:34]=2)[CH:24]=1.[OH-].[K+]>CO.O>[F:5][C:6]1[C:11]([CH:12]([OH:13])[C:37]2[C:31]3[C:32](=[N:33][CH:34]=[C:29]([C:25]4[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=4)[CH:30]=3)[NH:35][CH:36]=2)=[C:10]([F:14])[CH:9]=[CH:8][C:7]=1[OH:15]

Participants

7

Reactant 4

HCID 767Carbonic AcidHCID 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 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To carbonic acid tort-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-74fbb786d6684ee08528a3853536b9f2
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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