Dimethyl Sulfoxide → Methyl 2'-cyano-4'-methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylate

HRID 1845281Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:11]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[C:28]1[S:29][CH:30]=[CH:31][N:32]=1.CS(C)=O>CCOC(C)=O>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([O:16][C:28]2[S:29][CH:30]=[CH:31][N:32]=2)[CH:13]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[CH:11]=1)#[N:2]

Participants

Conditions

Temperature: 135 °C

Procedure

A stirred mixture of methyl 2′-cyano-5-hydroxy-4′-methylbiphenyl-3-carboxylate (350 mg, 1.2 mmol), potassium carbonate (363 mg, 2.63 mmol), 2-bromothiazole (431 mg, 2.63 mmol), and dimethyl sulfoxide (10 mL) was heated at 135° C. overnight. After cooling, the reaction mixture was diluted with EtOAc. The organic phase was washed with aq. NaHCO3 (sat.), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by flash chromatography to afford the title compound.

Workup

temperatureAfter cooling
washThe organic phase was washed with aq. NaHCO3 (sat.)
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-e11f49f983a74f3e822c4b20fcd06f6a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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