Methyl iodide → HCID 59375061, compound

HRID 661948Notes

Reaction equation

HRID 661948 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[C:28]2[C:27]3[C:22](=[CH:23][C:24]([OH:29])=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:19]([C:30]([NH2:32])=[O:31])=[CH:18][CH:17]=1>CS(C)=O.CCOC(C)=O>[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[C:28]2[C:27]3[C:22](=[CH:23][C:24]([O:29][CH3:1])=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:19]([C:30]([NH2:32])=[O:31])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59375146HCID 59375146, compound

Product 1

HCID 59375061HCID 59375061, compoundYield 9.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (25.1 mg, 0.182 mmol) and iodomethane (4.9 μL, 0.079 mmol) were added to a solution of 4-(2-fluorophenyl)-7-hydroxy-9H-carbazole-1-carboxamide (Example 40-1, 19.4 mg, 0.061 mmol) in DMSO (1 mL) and the mixture was stirred at rt. After 17 h, the mixture was diluted with EtOAc (30 mL), washed with saturated aqueous ammonium chloride (5 mL), water (2×5 mL), and brine (5 mL), dried and concentrated. The residue was purified by preparative HPLC to provide 4-(2-fluorophenyl)-7-methoxy-9H-carbazole-1-carboxamide (1.9 mg, 9%). 1H NMR (400 MHz, chloroform-d) δ 10.39 (1H, br. s.), 7.58 (1H, d, J=7.70 Hz), 7.44-7.55 (2H, m), 7.28-7.39 (2H, m), 7.07-7.22 (2H, m), 7.00 (1H, d, J=2.20 Hz), 6.65 (1H, dd, J=8.80, 2.42 Hz), 6.57 (2H, br. s.), 3.88 (3H, s). Mass spectrum m/z 335.0 (M+H)+.

Workup

  1. washwashed with saturated aqueous ammonium chloride (5 mL), water (2×5 mL), and brine (5 mL)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-157a1fadcc1048ea94cc7de9672ee28a
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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