Methyl iodide → HCID 67393677, compound

HRID 1776940Notes

Reaction equation

HRID 1776940 reaction equation
CI.[Br:3][C:4]1[C:5]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:9]([C:19]([NH:21][CH3:22])=[O:20])[C:8]=2[CH:23]=1.[C:29]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:3][C:4]1[C:5]([N:24]([CH3:29])[S:25]([CH3:28])(=[O:26])=[O:27])=[CH:6][C:7]2[O:11][C:10]([C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)=[C:9]([C:19]([NH:21][CH3:22])=[O:20])[C:8]=2[CH:23]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67393824HCID 67393824, compound

Product 1

HCID 67393677HCID 67393677, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

CH3I (31.6 g, 223 mmol) was added to a mixture of 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (32 g, 74 mmol), K2CO3 (25.6 g, 186 mmol) and KI (246 mg, 1.5 mmol) in DMF (150 mL) under N2 protection. The mixture was stirred at 80˜90° C. overnight. After concentrated in vacuo, the resulting residue was washed with water (200 mL) and EtOAc (200 mL) to provide the product of 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (31.5 g, 94%). 1H-NMR (CDCl3, 400 MHz) δ 8.16 (s, 1H), 7.88˜7.92 (m, 2H), 7.70 (s, 1H), 7.18˜7.23 (m, 2H), 5.78 (br s, 1H), 3.34 (s, 3H), 3.09 (s, 3H), 3.00 (d, J=4.8 Hz, 3H). MS (M+H)+: 455/457.

Workup

  1. concentrationAfter concentrated in vacuo
  2. washthe resulting residue was washed with water (200 mL) and EtOAc (200 mL)

Sources & evidence

ORD record
ord-b9d13298dcba4980af9c14254da61c2a
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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