Methyl iodide → HCID 67085886, compound

HRID 2036746Notes

Reaction equation

HRID 2036746 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]2[NH:7][C:6]3[CH2:19][CH:20]4[NH:24][CH:23]([C:5]=3[C:4]=2[C:3]=1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][CH2:21]4.[H-].[Na+].I[CH3:35]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]2[N:7]([CH3:35])[C:6]3[CH2:19][CH:20]4[NH:24][CH:23]([C:5]=3[C:4]=2[C:3]=1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][CH2:21]4

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67085251HCID 67085251, compound

Product 1

HCID 67085886HCID 67085886, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of step E (412 mg, 0.85 mmol) in DMF (10 mL) under a nitrogen atmosphere was added sodium hydride (60% dispersion in mineral oil, 69 mg, 1.70 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 1 h before addition of iodomethane (181 mg, 1.28 mmol). After stirring for an additional 2 h, the reaction mixture was quenched with water (50 mL) and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to give tert-butyl 2-bromo-4-benzyloxy-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (420 mg, 99%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.31-7.50 (m, 5H), 7.21-7.27 (m, 1H), 6.75 (d, J=1.2 Hz, 1H), 5.05-5.23 (m, 3H), 4.67 (br s, 1H), 3.79 (s, 3H), 3.32 (br s, 1H), 2.42 (d, J=15.9 Hz, 1H), 2.21-2.36 (m, 1H), 2.07-2.21 (m, 1H), 1.85-1.96 (m, 1H), 1.55-1.65 (m, 1H), 1.39 (br s, 9H).

Workup

  1. customthe reaction mixture was quenched with water (50 mL)
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f856c51b3910448b8d8f1947f1bcf793
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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