Carbon tetrabromide → 3-(2-bromoethyl)-2-(triethylsilyl)-5-(trifluoromethyl)-1H-indole

HRID 1918615노트

반응식

HRID 1918615 반응식
[CH2:1]([Si:3]([CH2:22][CH3:23])([CH2:20][CH3:21])[C:4]1[NH:5][C:6]2[C:11]([C:12]=1[CH2:13][CH2:14]O)=[CH:10][C:9]([C:16]([F:19])([F:18])[F:17])=[CH:8][CH:7]=2)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:43]C(Br)(Br)Br>C1COCC1>[Br:43][CH2:14][CH2:13][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:16]([F:19])([F:18])[F:17])[CH:10]=2)[NH:5][C:4]=1[Si:3]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:1][CH3:2]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 668320092-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol

생성물 1

HCID 668317303-(2-bromoethyl)-2-(triethylsilyl)-5-(trifluoromethyl)-1H-indole수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution 2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol (0.730 g; 2.13 mmol) in THF (6 mL) was added to a solution of triphenyl phosphine (0.836 g; 3.19 mmol) and perbromomethane (1.06 g; 3.19 mmol) in THF (12 mL) pre-stirred for 1 hour. The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was then filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 5 to 40% ethyl acetate in heptane) to afford 0.449 g (52%) of the title compound as a yellow oil.

후처리

  1. stirringThe resulting mixture was stirred at room temperature for 18 hours
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by flash chromatography on silica gel (eluent 5 to 40% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-27e2df3aa53a4e6eae636f4e71ea18d7
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618138B2

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