Trimethylsilyl iodide → 4-chloro-2-fluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide

HRID 1053153Notes

Reaction equation

[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([O:15]C)[CH:10]=2)=[O:7])=[C:4]([F:19])[CH:3]=1.[Si](I)(C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=2)=[O:7])=[C:4]([F:19])[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To 4-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide (4.35 g, 15.50 mmol) in acetonitrile (145.0 mL) was added TMSI (8.8 mL, 62.0 mmol). The reaction was stirred at 50° C. overnight. The acetonitrile was evaporated and the crude solid was triturated with ethyl acetate. The solid was isolated by filtration and washed with ethyl acetate to give 4-chloro-2-fluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide (3.8 g, 92%). ESI-MS m/z calc. 266.02. found 267.1 (M+1)+; Retention time: 1.23 minutes (3 minutes run). 1H NMR (400 MHz, DMSO-d6) δ 10.86 (s, 1H), 7.73 (t, J=8.0 Hz, 1H), 7.68 (dd, J=10.1, 1.9 Hz, 1H), 7.60 (d, J=7.1 Hz, 1H), 7.47 (dd, J=8.3, 2.0 Hz, 1H), 7.11 (d, J=2.0 Hz, 1H), 6.71 (dd, J=7.1, 2.1 Hz, 1H) ppm.

Workup

customThe acetonitrile was evaporated
customthe crude solid was triturated with ethyl acetate
customThe solid was isolated by filtration
washwashed with ethyl acetate

Sources & evidence

ORD record: ord-c174bf7ea4e1433992188b097a9ea2fc
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09393235B2

Reaction notes

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