Tributylvinyltin → 1-benzenesulfonyl-5-vinyl-1H-pyrrolo[2,3-b]pyridine

HRID 1515602노트

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HRID 1515602 반응식
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([Sn](CCCC)(CCCC)C=C)[CH2:21]CC>CN(C)C=O.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>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH:20]=[CH2:21])[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 2

HCID 81998TributylvinyltinHCID 242292461-Benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 672299711-benzenesulfonyl-5-vinyl-1H-pyrrolo[2,3-b]pyridine수율 87%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

A mixture of 1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridine (3.0 g, 8.9 mmol), tributyl-vinyl-stannane (3.9 mL, 13.55 mmol) and tetrakis(triphenylphosphine)palladium(0) (514 mg, 0.445 mmol) in N,N-dimethylformamide (10 mL) was stirred at 85° C. for 15 h. The mixture was cooled to 25° C., extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, hexanes to 15% ethyl acetate/hexanes) to afford 1-benzenesulfonyl-5-vinyl-1H-pyrrolo[2,3-b]pyridine (2.2 g, 87%) as a white solid: LC/MS m/e calcd for C15H13N2SO2 [M+H]+ 285.34, observed 285.2; 1H NMR (400 MHz, CDCl3) δ ppm 5.32 (d, J=11.0 Hz, 1H), 5.78 (d, J=17.6 Hz, 1H), 6.59 (d, J=4.0 Hz, 1H), 6.77 (dd, J=11.0 Hz, J=17.6 Hz, 1H), 7.49 (m, 2H), 7.58 (m, 1H), 7.74 (d, J=4.0 Hz, 1H), 7.88 (d, J=2.0 Hz, 1H), 8.19 (m, 2H), 8.46 (d, J=2.0 Hz, 1H).

후처리

  1. temperatureThe mixture was cooled to 25° C.
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, hexanes to 15% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-9d0f19c117cd4b93b4f088fab7476d45
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222416B2

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