Acetonitrile → tert-butyl 5-bromo-2,3-dihydro-1H-indole-1-carboxylate

HRID 856999Notes

Reaction equation

HRID 856999 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.[C:11]([O:15][C:16](=O)[O:17]C(C)(C)C)([CH3:14])([CH3:13])[CH3:12].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:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 34115665-BromoindolineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 21865438tert-butyl 5-bromo-2,3-dihydro-1H-indole-1-carboxylateYield 38%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromoindoline (3.96 g, 20 mmol), di-t-butylcarbonate (4.37 g, 20 mmol), 4-dimethylaminopyridine (2.69 g, 22 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 1 N 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 a solid. Trituration with hexane and drying in vacuo provided a white solid (2.26 g, 38% yield): 1H NMR (DMSO-d6, 300 MHz): 7.36 (s, 1H), 7.29 (d, 2H, J=7), 3.86 (t, 2H, J=7), 3.04 (t, 2H, J=7), 1.48 (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
  5. customto afford a solid
  6. dry with materialTrituration with hexane and drying in vacuo

Sources & evidence

ORD record
ord-8cdf484d100748838e5260d4bfacc2c9
Source dataset
uspto-grants-2006_12
Patent number
US07144894B2

Reaction notes

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