Potassium Phosphate, Tribasic → HCID 89826309, compound

HRID 625670Notes

Reaction equation

Br[C:2]1[C:3]([Cl:22])=[C:4]([CH2:9][C:10]([NH:12][C:13]2[N:14]=[CH:15][S:16][C:17]=2[C:18]([O:20][CH3:21])=[O:19])=[O:11])[C:5]([Cl:8])=[CH:6][CH:7]=1.[Cl:23][C:24]1[S:28][C:27](B(O)O)=[CH:26][CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:22][C:3]1[C:2]([C:27]2[S:28][C:24]([Cl:23])=[CH:25][CH:26]=2)=[CH:7][CH:6]=[C:5]([Cl:8])[C:4]=1[CH2:9][C:10]([NH:12][C:13]1[N:14]=[CH:15][S:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])=[O:11]

Participants

Conditions

Temperature: 180 °C

Procedure

300 mg (0.71 mmol) of methyl 4-{[(3-bromo-2,6-dichlorophenyl)acetyl]amino}-1,3-thiazole-5-carboxylate and 230 mg (1.41 mmol) of (5-chloro-2-thienyl)boronic acid were dissolved in a mixture of 18 ml of toluene and 3 ml of water, and 450 mg (2.12 mmol) of potassium phosphate, 15.9 mg (0.07 mmol) of palladium acetate and 20 mg (0.07 mmol) of tricyclohexylphosphine were added in succession. With microwave irradiation, the reaction mixture was then heated at 180° C. for 1 h. The mixture was filtered and the filtrate was taken up in ethyl acetate and water. The organic phase was dried and concentrated by evaporation. This gave 170 mg of methyl 4-({[2,6-dichloro-3-(5-chloro-2-thienyl)phenyl]acetyl}amino)-1,3-thiazole-5-carboxylate, which were reacted further without further purification.

Workup

additionwere added in succession
customWith microwave irradiation
filtrationThe mixture was filtered
customThe organic phase was dried
concentrationconcentrated by evaporation
customThis gave 170 mg of methyl 4-({[2,6-dichloro-3-(5-chloro-2-thienyl)phenyl]acetyl}amino)-1,3-thiazole-5-carboxylate, which were reacted further without further purification

Sources & evidence

ORD record: ord-641a684c188f4a9d81388288853ce57d
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09307767B2

Reaction notes

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