Hydrogen Bromide → HCID 58452414, compound

HRID 70586Notes

Reaction equation

Br.[Cl:2][C:3]1[C:4]([O:24]C)=[N:5][C:6](/[C:9](/[C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=2)=[CH:10]/[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:8]=1.O>O1CCOCC1>[Cl:2][C:3]1[C:4](=[O:24])[NH:5][C:6](/[C:9](/[C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=2)=[CH:10]/[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 85 °C

Procedure

48% hydrobromic acid (1.5 mL) was added to a solution of 3-chloro-6-{(E)-2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethenyl}-2-methoxypyridine (250 mg) in 1,4-dioxane (1.5 mL), and the mixture was stirred at 85° C. for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=9:1) to give a pale brown oil. This was powdered with a hexane/ethyl acetate solution, and filtration operation gave the title compound as a pale brown powder (230 mg, 71%).

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationafter which the filtrate was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=9:1)
customto give a pale brown oil
filtrationThis was powdered with a hexane/ethyl acetate solution, and filtration operation

Sources & evidence

ORD record: ord-19e945bda6ff4ebda70156bd3778bf86
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

Loading…