Triphenylphosphine → 2-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)cyclopropyI]ethyl bromide

HRID 1683977

반응식

HRID 1683977 반응식
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:22][C:23]1[CH:47]=[CH:46][C:26]([CH2:27][N:28]2[C:36]3[C:31](=[CH:32][C:33]([O:37][CH3:38])=[CH:34][CH:35]=3)[C:30]([C:39]3([CH2:42][CH2:43]O)[CH2:41][CH2:40]3)=[C:29]2[CH3:45])=[CH:25][CH:24]=1>C(Cl)Cl>[Br:22][C:23]1[CH:47]=[CH:46][C:26]([CH2:27][N:28]2[C:36]3[C:31](=[CH:32][C:33]([O:37][CH3:38])=[CH:34][CH:35]=3)[C:30]([C:39]3([CH2:42][CH2:43][Br:1])[CH2:41][CH2:40]3)=[C:29]2[CH3:45])=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 545542752-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl) cyclopropyl]ethanol

생성물 1

HCID 190417002-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)cyclopropyI]ethyl bromide수율 45.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

Bromine (136 mg, 0.85 mmol) was added to a-78° C. solution of triphenylphosphine (244 rag, 0.93 mmol) in 4 mL CH2Cl2, and the mixture was stirred 0.5 h at 0° C. and 5 rain at r.t. before recooling to -5° C. The alcohol from Step 8 (319 mg, 0.77 mmol) was then slowly added as a 1 mL CH2Cl2 solution and the mixture was stirred 2 h at 0° C. The reaction mixture was partitioned between CH2Cl2 and saturated NaHCO3. The organic layer was dried over MgSO4, concentrated and the residue purified by flash chromatography (10% ethyl acetate in hexane) to give 166 mg of the title compound.

후처리

  1. customat r.t.
  2. custombefore recooling to -5° C
  3. stirringthe mixture was stirred 2 h at 0° C
  4. customThe reaction mixture was partitioned between CH2Cl2 and saturated NaHCO3
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customthe residue purified by flash chromatography (10% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-daf665c75ff14761a40045b1545ca78c
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639780

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