Trimethylsilyl iodide → HCID 53379986, compound

HRID 625973Notes

Reaction equation

HRID 625973 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]([CH3:14])[C:12](=[O:15])[C:11]([O:16]C)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.I[Si](C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]([CH3:14])[C:12](=[O:15])[C:11]([OH:16])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 67418439HCID 67418439, compound

Product 1

HCID 53379986HCID 53379986, compoundYield 19.44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of crude 6-(4-chlorophenyl)-3-methoxy-1-methylpyridin-2(1H)-one in 5 mL acetonitrile was added iodotrimethylsilane (154 μL, 1.132 mmol) and the mixture was heated to 150° C. for 10 minutes. The reaction mixture was quenched with excess methanol, evaporated and purified using reversed-phase HPLC to afford 6-(4-chlorophenyl)-3-hydroxy-1-methylpyridin-2(1H)-one (17.3 mg, 19.44% yield).1H NMR (499 MHz, DMSO-d6): δ 7.68 (d, 1 H), 7.49 (dd, 1 H), 3.74 (s, 1 H), 2.54 (s, 1 H).

Workup

  1. customThe reaction mixture was quenched with excess methanol
  2. customevaporated
  3. custompurified

Sources & evidence

ORD record
ord-5d6cb13f2f48483a8acb8b4970992006
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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