Trimethylsilyl iodide → Ethyl 1-[6-(2-hydroxy-5-methylphenyl)-4-iodopyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1255206Notes

Reaction equation

HRID 1255206 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[O:15]C)[N:5]=[C:4]([N:17]2[C:21]([C:22]([F:25])([F:24])[F:23])=[C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:19]=[N:18]2)[CH:3]=1.I[Si](C)(C)C>C(Cl)(Cl)Cl>[OH:15][C:9]1[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=1[C:6]1[N:5]=[C:4]([N:17]2[C:21]([C:22]([F:24])([F:23])[F:25])=[C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:19]=[N:18]2)[CH:3]=[C:2]([I:1])[CH:7]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodide2×HCID 67158744Ethyl 1-[4-iodo-6-(2-methoxy-5-methylphenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 136356803Ethyl 1-[6-(2-hydroxy-5-methylphenyl)-4-iodopyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of the title compound from Example 19 Step F (1 g, 1.88 mmol) and iodotrimethylsilane (3.6 mL) in 15 mL chloroform was heated at 80° C. for 7 h. A second portion of iodotrimethylsilane (2 mL) was added and heating was continued at 90° C. overnight. The volatiles were removed in vacuo. Toluene was added, and the volatiles were removed in vacuo. Finally, dry MeOH was added, and the volatiles were removed in vacuo. Silica gel flash chromatography using hexanes:EtOAc (20:1 to pure EtOAc) gave the title compound: LCMS m/z 518.6 [M+H]+; 1H NMR (400 MHz, acetone-d6) δ 8.87 (d, J=1.1 Hz, 1H), 8.24 (s, 1H), 8.12 (d, J=1.1 Hz, 1H), 7.89 (d, J=2 Hz, 1H), 7.18 (dd, J=8.5, 2.0 Hz, 1H), 6.84 (d, J=8.3 Hz, 1H), 4.37 (q, J=7.1 Hz, 2H), 2.30 (s, 3H), 1.35 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureheating
  2. customThe volatiles were removed in vacuo
  3. additionToluene was added
  4. customthe volatiles were removed in vacuo
  5. additionFinally, dry MeOH was added
  6. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-64c32e8cfb6045369aaa1be64c16004e
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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