Water → 3-(5-Methyl-pyridin-2-yloxy)-benzonitrile

HRID 1034989Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].F[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]#[N:6])=[N:12][CH:13]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 3-hydroxy-benzonitrile (500 mg, 4.17 mmol), 2-fluoro-5-methylpyridine (467 mg, 4.17 mmol) and K2CO3 (150 mg) in N,N-dimethylformamide (5 mL) was heated at 150° C. overnight. The reaction mixture was poured into water, and extracted with ethyl acetate (2×). The solvent was removed, and the resulting residue was chromatographered using hexane/ethyl acetate (2:1) to give the title compound (315 mg, 36%). MS (DCI/NH3) m/z 211 (M4-1)+. 1HNMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 3 H) 7.02 (d, J=8.59 Hz, 1 H) 7.45 (ddd, J=8.29, 1.53, 0.92 Hz, 1 H) 7.61 (m, 3 H) 7.71 (ddd, J=8.29, 2.46, 0.61 Hz, 1 H) 7.99 (dt, J=2.45, 0.61 Hz, 1 H).

Workup

extractionextracted with ethyl acetate (2×)
customThe solvent was removed

Sources & evidence

ORD record: ord-65c958d295bc47dfaac704bd1a02c1a3
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546374B2

Reaction notes

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