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

HRID 1066757ノート

反応式

HRID 1066757 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-40 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4cbc253908044c1b964dc398948dca8b
出典データセット
uspto-grants-2001_06
特許番号
US06245769B1

反応ノート

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