Methyl Isocyanate → 5-Bromo-N-methyl-2,3-dihydro-1H-indole-1-carboxamide

HRID 2091604Notes

Reaction equation

HRID 2091604 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.CCN(C(C)C)C(C)C.[CH3:20][N:21]=[C:22]=[O:23]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:22]([NH:21][CH3:20])=[O:23])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 34115665-Bromoindoline

Product 1

HCID 123219725-Bromo-N-methyl-2,3-dihydro-1H-indole-1-carboxamideYield 72.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromoindoline (1.0 g, 5.05 mmol) and DIEA (1.9 mL, 11.11 mmol) in THF (40 mL) was added methylisocyanate (346 mg, 6.06 mmol). The reaction was maintained at room temperature for 4 h. The resulting precipitate was filtered and dried under vacuum to afford 5-bromo-N-methylindoline-1-carboxamide (935 mg, 72% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.75 (d, J=8.78 Hz, 1H), 7.17-7.31 (m, 2 H), 6.60 (d, J=4.27 Hz, 1H), 3.85 (t, J=8.78 Hz, 2H), 3.10 (t, J=8.66 Hz, 2H), 2.65 (d, J=4.27 Hz, 3H); MS (EI) m/z=255.1[M+1]+.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-d78eedd14a7c44b491fb216cf2ddde0a
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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