Hydrogen Bromide → 6-{(E)-1-(4-Chlorophenyl)-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-cyclopropylpyridin-2(1H)-one

HRID 70630Notes

Reaction equation

O1CCOCC1.Br.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](/[C:15](/[C:23]2[CH:28]=[CH:27][C:26]([CH:29]3[CH2:31][CH2:30]3)=[C:25]([O:32]C)[N:24]=2)=[CH:16]\[C@@H:17]2[NH:21][C:20](=[O:22])[CH2:19][CH2:18]2)=[CH:11][CH:10]=1>O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12](/[C:15](/[C:23]2[NH:24][C:25](=[O:32])[C:26]([CH:29]3[CH2:31][CH2:30]3)=[CH:27][CH:28]=2)=[CH:16]\[C@H:17]2[CH2:18][CH2:19][C:20](=[O:22])[NH:21]2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 65 °C

Procedure

1,4-Dioxane (4 mL) and 48% hydrobromic acid (2 mL) were added to (5R)-5-[(E)-2-(4-chlorophenyl)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one (250 mg), and the mixture was stirred at 65° C. for two hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0→90:10) to give the title compound as a colorless powder (65 mg, 68% (two steps)).

Workup

extractionfollowed by extraction with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0→90:10)

Sources & evidence

ORD record: ord-18ace6d546a04cda8fd5222d3300774f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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