Potassium Carbonate → HCID 131732286, compound

HRID 1424827Notes

Reaction equation

HRID 1424827 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH:13]1([C:16]2[C:17]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[CH:18][C:19]3[O:23][C:22]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)=[C:21]([C:31]([NH:33][CH3:34])=[O:32])[C:20]=3[CH:35]=2)[CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.CCOC(C)=O>[C:7]([C:6]1[CH:9]=[C:2]([N:36]([C:17]2[C:16]([CH:13]3[CH2:15][CH2:14]3)=[CH:35][C:20]3[C:21]([C:31]([NH:33][CH3:34])=[O:32])=[C:22]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[O:23][C:19]=3[CH:18]=2)[S:37]([CH3:40])(=[O:38])=[O:39])[CH:3]=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11])#[N:8]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 37564675-Fluoro-2-nitrobenzonitrileHCID 160735125-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide

Product 1

HCID 131732286HCID 131732286, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-fluoro-2-nitrobenzonitrile (1.280 mL, 11.18 mmol), 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (3.0 g, 7.45 mmol) and K2CO3 (3.09 g, 22.36 mmol) in 1,2-dimethoxyethane (30 mL) and water (7.5 mL) in a seal tube was heated to 80° C. overnight. It was cooled down to room temperature, diluted with EtOAc, filtered and the off-white solid was washed with water and then dried in vacuo to give crude desired product as a yellow solid (80% purity, 3.9 g, 76%). LCMS (m/z, ES+)=549 (M+H+)

Workup

  1. temperatureIt was cooled down to room temperature
  2. filtrationfiltered
  3. washthe off-white solid was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7c63d4111d684599b73771eb5e9874f2
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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