Methyl iodide → HCID 58093405, compound

HRID 474905Notes

Reaction equation

HRID 474905 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:16]=[C:15]2[C:7]([C:8]3[C:9](=[O:17])[CH2:10][CH2:11][CH2:12][C:13]=3[NH:14]2)=[CH:6][CH:5]=1.[CH3:18]I>CN(C=O)C>[Br:3][C:4]1[CH:16]=[C:15]2[C:7]([C:8]3[C:9](=[O:17])[CH2:10][CH2:11][CH2:12][C:13]=3[N:14]2[CH3:18])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58093392HCID 58093392, compound

Product 1

HCID 58093405HCID 58093405, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil, 0.342 g, 8.55 mmol) was added to a solution of 7-bromo-2,3-dihydro-1H-carbazol-4(9H)-one (2.46 g, 9.35 mmol) in DMF (33 mL) at room temperature under N2 and stirred for 15 min. Methyl iodide (1.99 mL, 14.0 mmol) was added to the solution, and the resulting solution was stirred for 2 h at ambient temperature. The mixture was quenched with H2O (80 mL), upon which a solid precipitated out of solution. The solids were collected by filtration and were washed thoroughly with water followed by hexanes to provide the title compound (2.43 g, 94%) as a tan solid: 1H NMR (500 MHz, DMSO-d6) δ 7.90 (d, J=8.5 Hz, 1H), 7.81 (d, J=1.5 Hz, 1H), 7.32 (dd, J=8.5, 1.5 Hz, 1H), 3.71 (s, 3H), 2.97 (t, J=6.0 Hz, 2H), 2.42 (t, J=6.0 Hz, 2H), 2.15-2.10 (m, 2H).

Workup

  1. stirringthe resulting solution was stirred for 2 h at ambient temperature
  2. customThe mixture was quenched with H2O (80 mL), upon which a solid
  3. customprecipitated out of solution
  4. filtrationThe solids were collected by filtration
  5. washwere washed thoroughly with water

Sources & evidence

ORD record
ord-4c42d1276e564865b967ee274f7e87df
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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