Methyl Acrylate → HCID 86650237, compound

HRID 1846960Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([C:22]([F:25])([F:24])[F:23])[N:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=3)[CH:8]=[CH:7][C:6]=12.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(CC)CC.[C:55]([O:59][CH3:60])(=[O:58])[CH:56]=[CH2:57]>CN(C=O)C>[F:19][C:18]([F:20])([F:21])[O:17][C:14]1[CH:13]=[CH:12][C:11]([C:9]2[CH:8]=[CH:7][C:6]3[N:5]([C:4]([C:22]([F:25])([F:24])[F:23])=[N:3][C:2]=3/[CH:57]=[CH:56]/[C:55]([O:59][CH3:60])=[O:58])[CH:10]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-bromo-6-(4-(trifluoromethoxy)phenyl)-3-(trifluoromethyl)imidazo[1,5-a]pyridine (50.0 mg, 0.118 mmol), Pd(AcO)2 (2.6 mg, 0.0118 mmol, 0.1 equiv.) and P(o-tol)3 (14.4 mg, 0.0472 mmol, 0.4 equiv.) were placed in a 50 mL round bottomed flask under a nitrogen atmosphere. To the flask were added DMF (1 mL), a solution of Et3N (30.0 mg, 0.295 mmol, 2.5 equiv.) in DMF (1 mL) and a solution of methyl acrylate (50.8 mg, 0.59 mmol, 5.0 equiv.) were successively added. The mixture was heated at 80° C. for 19 h. And then, the solvent was removed from the reaction mixture to give a crude mixture. The crude mixture was purified by a column chromatography (SiO2=25 g, EtOAc/hexane=1:7 to 1:3, Rf=0.1 with EtOAc/hexane=1:7) to give (E)-methyl 3-(6-(4-(trifluoromethoxy)phenyl)-3-(trifluoromethyl)imidazo[1,5-a]pyridin-1-yl)acrylate as light yellow crystals.

Workup

customAnd then, the solvent was removed from the reaction mixture
customto give a crude mixture
customThe crude mixture was purified by a column chromatography (SiO2=25 g, EtOAc/hexane=1:7 to 1:3, Rf=0.1 with EtOAc/hexane=1:7)

Sources & evidence

ORD record: ord-746ea432a55f44019425f05d85ad3db9
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952034B2

Reaction notes

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