Dimethylformamide → 4,5-Difluoro-2-(pyridin-2-yloxy)benzonitrile

HRID 2240394Notes

Reaction equation

Br[C:2]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[CH3:17][N:18](C)C=O>[C-]#N.[C-]#N.[Zn+2]>[F:16][C:12]1[C:13]([F:15])=[CH:14][C:2]([C:17]#[N:18])=[C:3]([O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=2)[CH:11]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of product of Example 136A (0.8 g, 2.76 mmol) in N,N-dimethylformamide (10 ml) were added Zn(CN)2 (0.18 g, 1.52 mmol) and Pd(Ph3)4 (0.32 g, 0.28 mmol) and stirred at 120° C. for overnight. The crude product was purified by flash column chromatography using 0%, 5% and 10% of ethylacetate in hexanes to yield 0.28 g (44%) of product. MS (ESI+) m/z 233 (M+H)+;

Workup

customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record: ord-0ac2081240d040baa8567ff58056857d
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723367B2

Reaction notes

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