Methyl iodide → HCID 67086028, compound

HRID 2036758Notes

Reaction equation

HRID 2036758 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:7]2[C:8]3[CH:17]4[NH:18][CH:14]([CH2:15][CH2:16]4)[CH2:13][C:9]=3[NH:10][C:11]=2[CH:12]=1.[CH3:26]I>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:7]2[C:8]3[CH:17]4[NH:18][CH:14]([CH2:15][CH2:16]4)[CH2:13][C:9]=3[N:10]([CH3:26])[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67173991HCID 67173991, compound

Product 1

HCID 67086028HCID 67086028, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (38 mg, 0.950 mmol) was added to a solution of the product of step A (240 mg, 0.636 mol) in DMF (4 mL) at room temperature under N2. After 1 h, methyl iodide (134 mg, 0.058 mL, 0.943 mol) was added, and the reaction allowed to proceed for an additional 1 h. The mixture was quenched with H2O, upon which a solid precipitated out of solution. The solids were filtered off to provide tert-butyl 3-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (248 mg, 100%) as a brown solid: 1H NMR (300 MHz, CDCl3) δ 7.40 (s, 1H), 7.35 (d, J=8.5 Hz, 1H), 7.19 (d, J=8.5 Hz, 1H), 5.30-5.10 (br m, 1H), 4.76-4.56 (br m, 1H), 3.54 (s, 3H), 3.49-3.19 (br m, 1H), 2.46 (d, J=16.0 Hz, 1H), 2.37-2.08 (m, 2H), 1.97-1.86 (m, 1H), 1.69-1.57 (m, 1H), 1.50 (s, 9H).

Workup

  1. waitto proceed for an additional 1 h
  2. customThe mixture was quenched with H2O, upon which a solid
  3. customprecipitated out of solution
  4. filtrationThe solids were filtered off

Sources & evidence

ORD record
ord-e4665ffa313e4b57895a9a46163a2010
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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