Tetrafluoroborate → 4-(3-Fluoro-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

HRID 1851172Notes

Reaction equation

[C:1]1([C:7]2[C:8]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=3)=[N:9][C:10]3[N:11]([CH:13]=[CH:14][N:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC[N+]12CC[N+]([F:34])(CC1)CC2.F[B-](F)(F)F>C(Cl)(Cl)Cl.O.ClCCl>[F:34][C:13]1[N:11]2[CH:12]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]([C:16]3[CH:17]=[CH:18][C:19]([CH:20]=[O:21])=[CH:22][CH:23]=3)=[N:9][C:10]2=[N:15][CH:14]=1

Participants

Conditions

Temperature: 120 °C

Procedure

500 mg 4-(6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde and 880 mg 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate were dissolved in 25 mL chloroform and heated under microwave irradiation to 120° C. After for 45 min and 4 h additional portions of 200 mg of 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate were added and heating continued at 120° C. The reaction was worked up after 5 h by diluting with water and extraction with dichloromethane. The combined organic layers were dried over Na2SO4 and the solvent evaporated. The crude material was purified on silica gel (dichloromethane/ethyl acetate.

Workup

temperatureheating
customcontinued at 120° C
waitThe reaction was worked up after 5 h
dry with materialThe combined organic layers were dried over Na2SO4
customthe solvent evaporated
customThe crude material was purified on silica gel (dichloromethane/ethyl acetate

Sources & evidence

ORD record: ord-990d56cb85f140f6b860dcb30d32466e
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957064B2

Reaction notes

Loading…