Acetonitrile → 2,6-dichloro-4-cyano-N-(pyridine-4-yl)benzamide

HRID 449874Notes

Reaction equation

[Cl:1][C:2]1[CH:16]=[C:15](I)[CH:14]=[C:13]([Cl:18])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:5].[C:19]([Cu])#[N:20].CC#N>CN(C=O)C>[Cl:1][C:2]1[CH:16]=[C:15]([C:19]#[N:20])[CH:14]=[C:13]([Cl:18])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:5]

Participants

Conditions

Temperature: 150 °C

Procedure

To the solution of 2,6-dichloro-4-iodo-N-(pyridin-4-yl)benzamide (0.15 g, 0.38 mmol) in DMF (2 mL) was added CuCN (0.17 g, 1.9 mmol). The mixture was heated at 150° C. under the irradiation of microwave for 1 hour. After the completion of the reaction, the mixture was filtered through Celite and purified by acid HPLC(YMC, 150 mm×30 mm, gradient: CH3CN/0.5% TFA, 10-50, 17 min) to afford the desired product (25.4 mg, yield: 23%). 1HNMR (DMSO-d6, 400 MHz): 611.95 (s, 1H), 8.74 (br, 2H), 8.33 (s, 2H), 7.97 (2H). LCMS (ESI) m/z: 292.1 [M+H+]

Workup

customAfter the completion of the reaction
filtrationthe mixture was filtered through Celite
custompurified by acid HPLC(YMC, 150 mm×30 mm, gradient

Sources & evidence

ORD record: ord-77368a9a18f24572a4d374e37721a3d4
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486950B2

Reaction notes

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