Trimethylsilyl iodide → HCID 86728471, compound

HRID 1053157Notes

Reaction equation

HRID 1053157 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([O:16]C)[CH:11]=2)=[O:8])=[C:5]([F:20])[CH:4]=1)#[N:2].[Si](I)(C)(C)C>C(#N)C>[C:1]([C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][NH:13][C:12](=[O:16])[CH:11]=2)=[O:8])=[C:5]([F:20])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86728470HCID 86728470, compound

Product 1

HCID 86728471HCID 86728471, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To 4-cyano-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide (7.3 g, 26.99 mmol) in acetonitrile (244.0 mL) was added TMSI (9.99 mL, 70.17 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-cyano-2-fluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide as a tan solid. ESI-MS m/z calc. 257.06. found 258.1 (M+1)+; Retention time: 1.08 minutes (3 minutes run). 1H NMR (400 MHz, DMSO-d6) δ 10.94 (s, 1H), 8.11 (t, J=11.4 Hz, 1H), 7.88 (m, 2H), 7.53 (d, J=7.1 Hz, 1H), 7.01 (d, J=2.0 Hz, 1H), 6.60 (dd, J=7.2, 2.1 Hz, 1H) ppm.

Workup

  1. customThe acetonitrile was evaporated
  2. customthe crude solid was triturated with ethyl acetate
  3. customThe solid was isolated by filtration
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-a1c0dd38f5e543bfb08077cc0351cf85
Source dataset
uspto-grants-2016_07
Patent number
US09393235B2

Reaction notes

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