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

HRID 856996Notes

Reaction equation

HRID 856996 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-502f0cdc74894bbeb7053cfc3283e59f
Source dataset
uspto-grants-2006_12
Patent number
US07144894B2

Reaction notes

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