HCID 66590713, compound → HCID 66590666, compound

HRID 1894831Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:21]=[CH:22]/[C:23]([O:25][CH3:26])=[O:24])[CH:9]=[CH:10][C:11]=1B1OC(C)(C)C(C)(C)O1)[CH2:2][CH2:3][CH3:4].Br[C:28]1[N:33]=[C:32]([N:34]([CH3:44])[C:35]([NH:37][C:38]2C=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:36])[CH:31]=[CH:30][CH:29]=1>CN(C)C=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:21]=[CH:22]/[C:23]([O:25][CH3:26])=[O:24])[CH:9]=[CH:10][C:11]=1[C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([N:34]([CH3:44])[C:35]([NH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[O:36])[N:33]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 90 °C

Procedure

496 mg of methyl(E)-3-[3-butoxy-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]acrylate are dissolved in 5 mL of dimethylformamide and 1 mL of 2N potassium phosphate solution. 350 mg of 1-(6-bromopyrid-2-yl)-1-methyl-3-phenylurea are added, along with 5 mg of palladium acetate and 16 mg of dicyclohexylbiphenylphosphine. The mixture is stirred for 3 hours at 90° C. and is then hydrolyzed and extracted with ethyl acetate. After evaporation of the solvents and chromatography on silica gel (eluent=7/3 heptane/ethyl acetate), 430 mg of methyl (E)-3-{3-butoxy-4-[6-(1-methyl-3-pentylureido)pyrid-2-yl]phenyl}acrylate are obtained. Yield=82%.

Workup

extractionhydrolyzed and extracted with ethyl acetate
customAfter evaporation of the solvents and chromatography on silica gel (eluent=7/3 heptane/ethyl acetate), 430 mg of methyl (E)-3-{3-butoxy-4-[6-(1-methyl-3-pentylureido)pyrid-2-yl]phenyl}acrylate
customare obtained

Sources & evidence

ORD record: ord-51a467aa445042159e56c224bf618fd0
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513297B2

Reaction notes

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