Triethylamine → 1-(4-Fluorophenyl)-4-oxo-6-vinyl-1,4-dihydroquinoline-3-carboxamide

HRID 1048874Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH:7]=[C:6]([C:19]([NH2:21])=[O:20])[C:5]2=[O:22].[CH2:23](N(CC)CC)[CH3:24].C([B-](F)(F)F)=C.[K+]>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[F:18][C:15]1[CH:16]=[CH:17][C:12]([N:8]2[C:9]3[C:4](=[CH:3][C:2]([CH:23]=[CH2:24])=[CH:11][CH:10]=3)[C:5](=[O:22])[C:6]([C:19]([NH2:21])=[O:20])=[CH:7]2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of compound E (450 mg, 1.25 mmol), triethylamine (174 μL, 1.25 mmol), and Pd(dppf)Cl2 CH2Cl2 (18.2 mg, 0.025 mmol) in 1-propanol (8.3 mL) was added potassium vinyltrifluoroborate (200 mg, 1.50 mmol). The reaction was purged with argon and stirred at 100° C. for 16 hours. The reaction was filtered over Celite® and washed very well with a 5% MeOH in DCM solution and concentrated in vacuo to give 385 mg (100%) of the title compound that was used without further purification. ES-MS [M+1]+: 309.2.

Workup

customThe reaction was purged with argon
filtrationThe reaction was filtered over Celite®
washwashed very well with a 5% MeOH in DCM solution
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e5f840f217304ec5b7bfcd11b89d1e2c
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382208B1

Reaction notes

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