Tributylphenyltin → 2-(4-Fluoro-phenyl)-4-hydroxy-1,3-diphenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642268노트

반응식

HRID 642268 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:14](Br)=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[C:30]1([Sn](CCCC)(CCCC)CCCC)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:14]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

참가 물질

6

반응물 2

HCID 607632TributylphenyltinHCID 684284133-bromo-2-(4-fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

생성물 1

HCID 684285202-(4-Fluoro-phenyl)-4-hydroxy-1,3-diphenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester수율 33%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
130 °C

실험 절차

A mixture of 3-bromo-2-(4-fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (180 mg, 0.395 mmol), phenyltributlytin (149 μL, 0.454 mmol), and Pd(PPh3)2Cl2 (14 mg, 0.020 mmol) in DMF (2 mL) was stirred at 130° C. overnight. Then the mixture was diluted with EtOAc, washed with water and saturated NaCl aqueous solution respectively; the EtOAc phase was dried over anhydrous sodium sulfate, concentrated, the residue was purified by column and prep TLC to give a white solid, the desired title compound (59 mg). The title compound, ESI MS (m/z): 453 (M+H+).

후처리

  1. washwashed with water and saturated NaCl aqueous solution respectively
  2. dry with materialthe EtOAc phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customthe residue was purified by column
  5. customto give a white solid

출처 및 근거

ORD 기록
ord-bdc20afe24e94f2b97a5fcd2c6f6476f
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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