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

HRID 1964973
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HRID 1964973 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 962Water용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-74fbb786d6684ee08528a3853536b9f2
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415469B2

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