Sodium Carbonate → HCID 131732314, compound

HRID 1424865Notes

Reaction equation

HRID 1424865 reaction equation
[CH:1]1([C:4]2[C:5]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]([NH:21][CH3:22])=[O:20])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1.[F:29][C:30]1[C:31]([N+:41]([O-:43])=[O:42])=[C:32]([CH:37]=[C:38](F)[CH:39]=1)[C:33]([O:35][CH3:36])=[O:34].C([O-])([O-])=O.[Na+].[Na+]>CN(C)P(N(C)C)(N(C)C)=O.CCOC(C)=O>[CH:1]1([C:4]2[C:5]([N:24]([C:38]3[CH:39]=[C:30]([F:29])[C:31]([N+:41]([O-:43])=[O:42])=[C:32]([CH:37]=3)[C:33]([O:35][CH3:36])=[O:34])[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19](=[O:20])[NH:21][CH3:22])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 160735125-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamideHCID 46311132Methyl 3,5-difluoro-2-nitrobenzoate

Product 1

HCID 131732314HCID 131732314, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (1.850 g, 4.60 mmol), methyl 3,5-difluoro-2-nitrobenzoate (1.996 g, 9.19 mmol) and Na2CO3 (1.462 g, 13.79 mmol) in hexamethylphosphoramide (25 mL) was stirred overnight at room temperature. The mixture was diluted with EtOAc and filtered through a pad of Celite®. The filtrate was washed with brine, dried over Na2SO4, concentrated and purified by silica gel chromatography (0-35% EtOAc in hexanes) to give methyl 5-(N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)-3-fluoro-2-nitrobenzoate (1.61 g, 58% yield) as yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.62 (br. s., 1H), 0.79-0.95 (m, 2H), 0.96-1.11 (m, 1H), 1.84-1.97 (m, 1H), 3.01 (d, J=5.0 Hz, 3H), 3.31-3.36 (m, 3H), 3.87 (s, 3H), 5.82 (d, J=4.6 Hz, 1H), 7.22 (t, J=8.6 Hz, 2H), 7.37-7.44 (m, 1H), 7.50-7.54 (m, 2H), 7.56 (s, 1H), 7.83-7.92 (m, 2H). LCMS (m/z, ES+)=600.2 (M+H+).

Workup

  1. filtrationfiltered through a pad of Celite®
  2. washThe filtrate was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0-35% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c3fe18087ab14373a0930668959b53d5
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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