Methyl iodide → HCID 58093399, compound

HRID 474896Notes

Reaction equation

HRID 474896 reaction equation
[C:1]([O-])([O-])=O.[Cs+].[Cs+].IC.[Br:9][C:10]1[CH:22]=[C:21]2[C:13]([C:14]3[CH2:15][CH2:16][CH2:17][C:18](=[O:23])[C:19]=3[NH:20]2)=[CH:12][CH:11]=1>CN(C=O)C.O>[Br:9][C:10]1[CH:22]=[C:21]2[C:13]([C:14]3[CH2:15][CH2:16][CH2:17][C:18](=[O:23])[C:19]=3[N:20]2[CH3:1])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 57941535847987-95-5

Product 1

HCID 58093399HCID 58093399, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Cs2CO3 (2.5 g, 7.5 mmol) and iodomethane (0.47 mL, 7.5 mmol) were added to a solution of 7-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one (1.7 g, 6.3 mmol) in DMF (21 mL), and the resulting mixture was stirred for 4 h at ambient temperature. The reaction was diluted with H2O (25 mL), and the resulting solution was stirred for 15 minutes. The resulting precipitate was collected by filtration, washed with H2O (200 mL) and dried to yield the title compound (1.5 g, 87%) as an off-white powder: 1H NMR (500 MHz, DMSO-d6) δ 7.83 (d, J=1.5 Hz, 1H), 7.67 (d, J=8.5 Hz, 1H), 7.25 (dd, J=8.5, 1.5 Hz, 1H), 3.98 (s, 3H), 2.96 (t, J=6.0 Hz, 2H), 2.57 (t, J=6.0 Hz, 2H), 2.13-2.10 (m, 2H).

Workup

  1. stirringthe resulting solution was stirred for 15 minutes
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with H2O (200 mL)
  4. customdried

Sources & evidence

ORD record
ord-b11bf9d347a34095a38a4948de3adf46
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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