Allyl bromide → HCID 58026901, compound

HRID 1966291Notes

Reaction equation

[C:1]([O:5][CH2:6][C:7]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9]([CH3:27])=[CH:10][C:11]([CH3:26])([CH3:25])[NH:12]2)(=[O:4])[CH:2]=[CH2:3].[CH2:28](Br)[CH:29]=[CH2:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][CH2:6][C:7]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9]([CH3:27])=[CH:10][C:11]([CH3:26])([CH3:25])[N:12]2[CH2:30][CH:29]=[CH2:28])(=[O:4])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5-acryloyloxymethyl-6-(2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-7, 50 mg, 0.14 mmol), allylbromide (111 μL, 1.28 mmol) and potassium carbonate (78 mg, 0.56 mmol) was suspended in anhydrous N,N-dimethylformamide (2 mL), and the reaction mixture was stirred at 60° C. for 4 days. After cooling down, it was diluted with ethyl acetate (25 mL). The whole was washed with water (30 mL, twice) and saturated brine (30 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (23 mg) as a pale yellow oil. (Yield 41%)

Workup

temperatureAfter cooling down
washThe whole was washed with water (30 mL
dry with materialtwice) and saturated brine (30 mL) successively, dried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-143f10f5964f459d90a6b8bc01b61524
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420635B2

Reaction notes

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