Benzyl Bromide → HCID 57690537, compound

HRID 401499Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[C:9]([C:10]([C:12]2[N:13]=[CH:14][NH:15][CH:16]=2)=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1.C(OCC)(=O)C>[CH2:17]([N:15]1[CH:16]=[C:12]([C:10]([C:9]2[C:4]([F:3])=[N:5][CH:6]=[CH:7][CH:8]=2)=[O:11])[N:13]=[CH:14]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60% in mineral oil, 23 mg, 0.58 mmol) was added to a solution of (2-fluoropyridin-3-yl)(1H-imidazol-4-yl)methanone (100 mg, 0.52 mmol) in tetrahydrofuran (3 ml), cooled to 0° C. The reaction mixture was then stirred for 30 minutes. Benzyl bromide (0.062 ml, 0.52 mmol) was added and the mixture was warmed up to room temperature. The reaction mixture was stirred for 18 hours, diluted with ethyl acetate and washed with a saturated aqueous solution of sodium bicarbonate and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound (100 mg, 68% yield).

Workup

temperaturethe mixture was warmed up to room temperature
stirringThe reaction mixture was stirred for 18 hours
washwashed with a saturated aqueous solution of sodium bicarbonate and brine
dry with materialThe organic phase was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record: ord-b58e97239e914ce8b25d5a9fd9ab2b26
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741931B2

Reaction notes

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