Acetonitrile → 5-Bromo-2-methyl-1-t-butyloxycarbonylindole

HRID 856996노트

반응식

HRID 856996 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[CH:5]2.[C:12]([O:16][C:17](=O)[O:18]C(C)(C)C)([CH3:15])([CH3:14])[CH3:13].CC#N>CN(C)C1C=CN=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[C:6]([CH3:11])=[CH:5]2

참가 물질

6

반응물 3

HCID 6342AcetonitrileHCID 50039685-Bromo-2-methylindoleHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

생성물 1

HCID 218654515-Bromo-2-methyl-1-t-butyloxycarbonylindole수율 99%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8857Ethyl Acetate용매

실험 절차

5-Bromo-2-methylindole (4.2 g, 200.0 mmol), di-t-butylcarbonate (4.37 g, 20 mmol), 4-dimethylaminopyridine (2.93 g, 24 mmol) and CH3CN (50 mL) were mixed and stirred at room temperature for 16 h. The reaction mixture was diluted with EtOAc (300 mL) and the organic solution was washed successively with water (50 mL), a 1N HCl solution (50 mL), a saturated NaHCO3 solution (2×50 mL) and brine (25 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford an oil (6.11 g, 99% yield): 1H NMR (CDCl3, 300 MHz): 7.98 (d, 1H, J=9), 7.56 (d, 1H, J=1), 7.32 (dd, H, J=9, 1), 6.27 (s, 1H), 2.60 (d, 3H, J=1), 1.69 (s, 9H).

후처리

  1. washthe organic solution was washed successively with water (50 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-502f0cdc74894bbeb7053cfc3283e59f
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144894B2

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