Cesium fluoride → 7-methoxy-3-(2-phenoxyphenyl)-1H-pyrrolo[2,3-c]pyridine

HRID 633514

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HRID 633514 반응식
I[C:2]1[C:10]2[C:5](=[C:6]([O:11][CH3:12])[N:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[O:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[F-].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>[CH3:12][O:11][C:6]1[N:7]=[CH:8][CH:9]=[C:10]2[C:2]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[O:13][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:3][NH:4][C:5]=12

참가 물질

6

반응물 3

HCID 25953Cesium fluorideHCID 2773559(2-Phenoxyphenyl)boronic acidHCID 534127193-Iodo-7-methoxy-1H-pyrrolo[2,3-c]pyridine

생성물 1

HCID 904166737-methoxy-3-(2-phenoxyphenyl)-1H-pyrrolo[2,3-c]pyridine수율 38.6%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매

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온도
120 °C

실험 절차

A mixture of 3-iodo-7-methoxy-1H-pyrrolo[2,3-c]pyridine (0.274 g, 1.0 mmol), 2-phenoxyphenylboronic acid (0.278 g, 1.3 mmol, 1.3 equivalents), Pd(PPh3)4 (0.058 g, 0.05 mmol), and cesium fluoride (0.456 g, 3 mmol) in dimethxoyethane (3 mL) and methanol (1.5 mL) was heated under microwave conditions (120° C., 30 minutes). The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 30% ethyl acetate/hexanes) to give the title compound (0.122 g, 38.6% yield).

후처리

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica gel, 30% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-c490091761d54383a603ffe9a2da55ae
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321764B2

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