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

HRID 856996ノート

反応式

HRID 856996 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 218654515-Bromo-2-methyl-1-t-butyloxycarbonylindole収率 99%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-502f0cdc74894bbeb7053cfc3283e59f
出典データセット
uspto-grants-2006_12
特許番号
US07144894B2

反応ノート

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