Sodium hydride → tert-butyl 2-bromo-3-cyclohexyl-1-(2-methoxy-2-oxoethyl)-1H-indole-6-carboxylate

HRID 1714005노트

반응식

HRID 1714005 반응식
[H-].[Na+].Br[CH2:4][C:5]([O:7][CH3:8])=[O:6].[Br:9][C:10]1[NH:11][C:12]2[C:17]([C:18]=1[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[CH:16][CH:15]=[C:14]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:13]=2>>[Br:9][C:10]1[N:11]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:12]2[C:17]([C:18]=1[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[CH:16][CH:15]=[C:14]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:13]=2

참가 물질

4

반응물 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 59750072tert-Butyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate2회

생성물 1

HCID 68511006tert-butyl 2-bromo-3-cyclohexyl-1-(2-methoxy-2-oxoethyl)-1H-indole-6-carboxylate수율 80%

실험 절차

NaH (1.4 eq, 60% dispersion in mineral oil) was added to a solution of tert-butyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate in DMF (from Step 5, 0.15 M) and the solution stirred at RT for 30 min. Then methyl bromoacetate (1.4 eq) was added and the mixture stirred at RT for 3 h. The solvent was removed in vacuo and the residue taken up in EtOAc. The organic phase was washed twice with aqueous HCl (0.5 N) and then brine. The organic phase was dried over Na2SO4, filtered and the solvent evaporated in vacuo. The residue was purified by crystallisation (EtOAc/PE) to afford the title compound (80%); MS (ES+) m/z 450 (M+H)+, m/z 452 (M+H)+.

후처리

  1. stirringthe mixture stirred at RT for 3 h
  2. customThe solvent was removed in vacuo
  3. washThe organic phase was washed twice with aqueous HCl (0.5 N)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified by crystallisation (EtOAc/PE)

출처 및 근거

ORD 기록
ord-98994e008d0144688176e863f998dfb6
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795247B2

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