Potassium Carbonate → 4-((6-Bromopyridin-3-yl)oxy)benzonitrile

HRID 63252

Reaction equation

[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.F[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-bromopyridin-3-ol (10 g, 57.80 mmol) in DMF (60 mL) was added 4-fluorobenzonitrile (6.99 g, 57.8 mmol) and K2CO3 (11.9 g, 86.70 mmol) and the reaction mixture was stirred at 80° C. for 16 hours (h). The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated. The crude product was purified by column chromatography (silica gel, 100-200 mesh) to obtain the title compound as an off-white solid (10 g, 63%): mp 113° C.; 1H NMR (400 MHz, CDCl3) δ 8.22 (d, J=2.9 Hz, 1H), 7.70-7.63 (m, 2H), 7.56-7.51 (m, 1H), 7.28 (dd, J=8.5, 2.9 Hz, 1H), 7.10-7.02 (m, 2H); EIMS m/z 275.

Workup

extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over sodium sulphate
concentrationconcentrated
customThe crude product was purified by column chromatography (silica gel, 100-200 mesh)

Sources & evidence

ORD record: ord-e8fee109147d4865ad47f6b30b8a68c8
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447073B2

Linked notes

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