Trimethylsilyl isocyanate → HCID 11404049, compound

HRID 1437531Notes

Reaction equation

HRID 1437531 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH2:15])[CH2:8][CH2:7][CH2:6][C:5]2=1.C[Si]([N:20]=[C:21]=[O:22])(C)C>C(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH:15][C:21]([NH2:20])=[O:22])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 5978796-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Product 1

HCID 11404049HCID 11404049, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine (50 mg, 0.19 mmol) in isopropanol (0.30 mL) was added trimethylsilyl isocyanate. The mixture was stirred at room temperature 15 hours, the solvent removed, and the residue purified by flash chromatography (0-5% methanol-dichloromethane) to give 23 mg (40% yield) of a brown solid. 1H-NMR (DMSO-d6): δ 10.91 (s, 1H), 7.57 (d, 1H), 7.30 (d, 1H), 7.16 (dd, 1H), 6.46 (d 1H), 4.87 (m, 1H), 2.64 (m, 2H), 1.97 (m, 1H), 1.90-1.65 (m, 3H); MS m/z 308 (M−1).

Workup

  1. customthe solvent removed
  2. customthe residue purified by flash chromatography (0-5% methanol-dichloromethane)

Sources & evidence

ORD record
ord-4fc2abcca1cd4fabad212a05801c9708
Source dataset
uspto-grants-2009_11
Patent number
US07622494B2

Reaction notes

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