Cesium carbonate → HCID 67017328, compound

HRID 1842036Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:15])/[CH:5]=[CH:6]/[C:7]1[C:12]([NH2:13])=[CH:11][CH:10]=[C:9](Br)[N:8]=1)[CH3:2].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[CH2:1]([O:3][C:4](=[O:15])/[CH:5]=[CH:6]/[C:7]1[C:12]([NH2:13])=[CH:11][CH:10]=[C:9]([C:21]2[CH:22]=[CH:23][C:18]([C:17]([F:28])([F:27])[F:16])=[CH:19][CH:20]=2)[N:8]=1)[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

3.0 g (E)-3-(3-Amino-6-bromo-pyridin-2-yl)-acrylic acid ethyl ester, 3.05 g 4-(Trifluoromethyl)phenylboronic acid and 3.61 g cesium carbonate were dissolved in a mixture of 21 ml dimethylformamide and 7 ml water. An argon stream was bubbled through the reaction mixture for thirty minutes then 333 mg Tetrakis(tripehnylphosphine)palladium(0) were added and the reaction mixture stirred at 110° C. for 1.5 hours. The reaction mixture was diluted by addition of 50 ml water and extracted three times with portions of 80 ml dichloromethane. The combined organic layers were dried over MgSO4 then the solvent was removed in vacuo. The residue was purified by chromatography on silica gel to obtain 2.4 g (E)-3-[3-Amino-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]acrylic acid ethyl ester.

Workup

customAn argon stream was bubbled through the reaction mixture for thirty minutes
addition333 mg Tetrakis(tripehnylphosphine)palladium(0) were added
additionThe reaction mixture was diluted by addition of 50 ml water
extractionextracted three times with portions of 80 ml dichloromethane
dry with materialThe combined organic layers were dried over MgSO4
customthe solvent was removed in vacuo
customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-aa86bc7766094e8086bd38493a8df9a1
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946212B2

Reaction notes

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