3-Bromo-4-cyclopropyl-5-fluoropyridine → 4-Cyclopropyl-5-fluoronicotinonitrile

HRID 717542Notes

Reaction equation

[Cu]([C:4]#[N:5])C#N.Br[C:7]1[CH:8]=[N:9][CH:10]=[C:11]([F:16])[C:12]=1[CH:13]1[CH2:15][CH2:14]1>CN(C)C=O>[CH:13]1([C:12]2[C:7]([C:4]#[N:5])=[CH:8][N:9]=[CH:10][C:11]=2[F:16])[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 150 °C

Procedure

Copper cyanide (0.829 g, 0.00925 mol) was added at RT to a sealed tube containing 3-bromo-4-cyclopropyl-5-fluoro-pyridine (B; 1 g, 0.00462 mol) in dimethylformamide (20 mL). The reaction mixture was heated to 150° C. for 18 hr, then cooled to RT, quenched with 20% aqueous ammonia (20 mL) solution, and stirred for 5 min. It was extracted with diethyl ether (2×100 mL). The combined organic layers were washed with water (2×50 mL) and dried over anhydrous sodium sulphate to afford 4-cyclopropyl-5-fluoronicotinonitrile. MS (M+1): 163.1.

Workup

temperaturecooled to RT
customquenched with 20% aqueous ammonia (20 mL) solution
extractionIt was extracted with diethyl ether (2×100 mL)
washThe combined organic layers were washed with water (2×50 mL)
dry with materialdried over anhydrous sodium sulphate

Sources & evidence

ORD record: ord-3ffa4e63a74b4c1089b482f2fbd563ba
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193724B2

Reaction notes

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