Trimethylsilyl iodide → HCID 178426047, compound

HRID 1501125Notes

Reaction equation

HRID 1501125 reaction equation
C[O:2][C:3]1[C:8]([CH2:9][NH:10][C:11](=[O:25])[C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=[C:7]([C:26]([F:29])([F:28])[F:27])[CH:6]=[C:5]([CH3:30])[N:4]=1.I[Si](C)(C)C>C(#N)C>[OH:2][C:3]1[C:8]([CH2:9][NH:10][C:11](=[O:25])[C:12]2[CH:13]=[CH:14][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:16][CH:17]=2)=[C:7]([C:26]([F:28])([F:27])[F:29])[CH:6]=[C:5]([CH3:30])[N:4]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 89580991HCID 89580991, compound

Product 1

HCID 178426047HCID 178426047, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-((2-methoxy-6-methyl-4-(trifluoromethyl)pyridin-3-yl)methyl)-4-phenoxybenzamide (0.12 g, 0.3 mmol) in anhydrous acetonitrile (20 mL) was added iodotrimethylsilane (200 mg, 1 mmol). Then the mixture was stirred at room temperature for 2 hours. Then the reaction mixture was concentrated to give a residue and the residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1) to give the pure product N-((2-hydroxy-6-methyl-4-(trifluoromethyl)pyridin-3-yl)methyl)-4-phenoxybenzamide (90 mg, 75%). LRMS (M+H) m/z: calcd 402.12. found 402. HPLC purity (214 nm): 98%. 1H NMR (300 MHz, CD3OD): δ 7.79-7.77 (m, 2H), 7.42-7.37 (m, 2H), 7.18 (t, J=6.3 Hz, 1H), 7.04 (d, J=7.5 Hz, 2H), 6.97 (d, J=7.8 Hz, 2H), 6.40 (s, 1H), 4.57 (s, 2H), 2.36 (s, 3H).

Workup

  1. concentrationThen the reaction mixture was concentrated
  2. customto give a residue
  3. customthe residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1)

Sources & evidence

ORD record
ord-966c98ba9ce740548974c6587c640d62
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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