Tributylvinyltin → 1-[(4-Methylphenyl)sulfonyl]-4-vinyl-1H-indole

HRID 1159753

반응식

HRID 1159753 반응식
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[CH2:21]([Sn](CCCC)(CCCC)C=C)[CH2:22]CC>C1(C)C=CC=CC=1>[CH3:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([N:6]2[C:7]3[C:3](=[C:2]([CH:21]=[CH2:22])[CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:5]2)(=[O:13])=[O:12])=[CH:15][CH:16]=1

참가 물질

4

반응물 2

HCID 81998TributylvinyltinHCID 5628694-Bromo-1-(toluene-4-sulfonyl)-1H-indole2회

생성물 1

HCID 124465911-[(4-Methylphenyl)sulfonyl]-4-vinyl-1H-indole수율 77%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

4-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indole (600 mg, 1.71 mmol; Intermediate 3), tributyl(vinyl)stannane (0.550 mL, 1.88 mmol) and Pd(PPh3)2OAc2 (32 mg, 0.043 mmol) were mixed in dry toluene (8 mL) and stirred 24 h at 110° C. using a STEM block, then rt. for 40 h. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (20% DCM in hexane-50% DCM in hexane). This afforded the title compound 390 mg, 77% as a colorless sticky oil. MS (ESI+) for C17H15NO2S m/z 298 (M+H)+.

후처리

  1. customrt
  2. waitfor 40 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography (20% DCM in hexane-50% DCM in hexane)

출처 및 근거

ORD 기록
ord-8bf2c7966f23436ab574bd4a6fd7898f
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812017B2

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