1,2-Dibromoethane → 1h-Indole-1-carboxylic acid,7-bromo-2,3-dihydro-5-methoxy-,1,1-dimethylethyl ester

HRID 1060625노트

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HRID 1060625 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(CCN(C)C)C.[Li]C(CC)C.[Br:32]CCBr>CCOCC>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][C:15]=2[Br:32])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 78391,2-DibromoethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 105147621,1-Dimethylethyl 2,3-dihydro-5-methoxy-1H-indole-1-carboxylateHCID 178418400CID 53628100

생성물 1

HCID 186292191h-Indole-1-carboxylic acid,7-bromo-2,3-dihydro-5-methoxy-,1,1-dimethylethyl ester

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-40 °C

실험 절차

Part C: To 1-(tert-Butoxycarbonyl)-5-methoxyindoline (2.0 g) and TMEDA (1.57 mL, 1.3 eq.) in ether (40 mL) at −78° C. was added sec-BuLi (7.4 mL, 1.2 eq.). The reaction was warmed to −40° C. for 2 hours and then cooled to −78° C. 1,2-dibromoethane (2.07 mL, 3 eq.) was added and the reaction stirred for 45 minutes at −78° C. The bath was then removed and the reaction was stirred for 1 hour. The reaction was quenched with water and extracted with ether. The ether was washed with brine, dried over MgSO4, and concentrated. The crude product was chromatographed on silica gel, using hexane/ethyl acetate (19:1) as eluent, affording 1-(tert-butoxycarbonyl)-7-bromo-5-methoxyindoline (1.16 g).

후처리

  1. temperaturecooled to −78° C
  2. customThe bath was then removed
  3. stirringthe reaction was stirred for 1 hour
  4. customThe reaction was quenched with water
  5. extractionextracted with ether
  6. washThe ether was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe crude product was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-1801c603c8824861a2fa39ccbe0bfee7
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525056B2

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