Sodium hydride → 1-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-5-bromopyridin-2(1H)-one

HRID 336629Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

To an ambient suspension of NaH (185 mg, 4.63 mmol, 60% dispersion in mineral oil) in N,N-dimethylformamide (30 mL) was added 5-bromopyridin-2(1H)-one (700 mg, 4.02 mmol). The reaction mixture was stirred for 15 minutes, and 1-(bromomethyl)adamantane (968 mg 4.22 mmol) was added. The mixture was heated to 120° C. overnight, cooled to room temperature, and quenched by the addition of water and ether. The layers were separated, and the aqueous extracted with additional ether (twice). The combined organics were washed with brine, dried over Na2SO4, and filtered. Chromatography on silica gel, eluting with a gradient of 5 to 30% ethyl acetate in hexanes, provided the title compound.

Workup

temperaturecooled to room temperature
customquenched by the addition of water and ether
customThe layers were separated
extractionthe aqueous extracted with additional ether (twice)
washThe combined organics were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
washChromatography on silica gel, eluting with a gradient of 5 to 30% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-520b6d60f81244c98b4b95ecbb87bff4
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889675B2

Reaction notes

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