Dimethylformamide → HCID 67284590, compound

HRID 1618654Notes

Reaction equation

Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[C:16]1([C:22](B2OC(C)(C)C(C)(C)O2)=[CH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>CCOC(C)=O.[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH2:23])[C:11]=1[CH3:12]

Participants

Conditions

Temperature: 95 °C

Procedure

A screw cap vial was charged with 2,4-dichloro-5,7-difluoro-3-methylquinoline (99 mg, 0.398 mmol), 1-phenylvinylboronic acid pinacol ester (110 mg, 0.478 mmol), dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium(II) (32.5 mg, 0.040 mmol), potassium carbonate (165 mg, 1.195 mmol), and DMF (3.98 mL), and the mixture was heated at 95° C. under a N2 atmosphere for 18 h. The reaction was then cooled to rt, diluted with EtOAc, and washed with water and brine. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography, eluting with a gradient of 0-10% EtOAc in hexane to give 4-chloro-5,7-difluoro-3-methyl-2-(1-phenylvinyl)-quinoline as an orange solid. Mass Spectrum (ESI) m/e=316.0 (M+1).

Workup

customA screw cap vial
temperatureThe reaction was then cooled to rt
washwashed with water and brine
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated under reduced pressure
customThe crude product was purified by flash chromatography
washeluting with a gradient of 0-10% EtOAc in hexane

Sources & evidence

ORD record: ord-ffb918cefec943de9da1394f4ca252c6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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