1,2-Dimethoxyethane → HCID 118113432, compound

HRID 713675Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([S:23]([CH2:26][CH3:27])(=[O:25])=[O:24])[C:5]([C:8]([N:10]([CH3:22])[C:11]2[CH:16]=[CH:15][C:14]([S:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[O:9])=[N:6][CH:7]=1.[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(COC)OC>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:26]([S:23]([C:4]1[C:5]([C:8]([N:10]([CH3:22])[C:11]2[CH:16]=[CH:15][C:14]([S:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[O:9])=[N:6][CH:7]=[C:2]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:3]=1)(=[O:25])=[O:24])[CH3:27]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 250 mg of 5-chloro-3-ethylsulfonyl-N-methyl-N-(4-trifluoromethylsulfanylphenyl)picolinamide (Compound of Present Invention 118), 104 mg of phenylboronic acid, 10 mg of tris(dibenzylideneacetone)dipalladium(0), 25 mg of 2-dicyclohexylphosphino-2′-4′-6′-triisopropylphenyl, 242 mg of tripotassium phosphate and 3 ml of dimethoxyethane was stirred at 70° C. for 3 hours. Water was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 112 mg of 3-ethylsulfonyl-5-phenyl-N-methyl-N-(4-trifluoromethylsulfanylphenyl)picolinamide (hereinafter, referred to as Compound of Present Invention 124).

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c6fd5d467eb1457b94d37a1c3db08189
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09185910B2

Reaction notes

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