Iodine → Ethyl 1-[6-(2-hydroxy-3-iodophenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 340627

Reaction equation

HRID 340627 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([N:14]2[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]2)[CH:11]=[CH:10][CH:9]=1.[I:28]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[OH:1][C:2]1[C:7]([I:28])=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([N:14]2[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]2)[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 807IodineHCID 136298134Ethyl 1-[6-(2-hydroxylphenyl)pyridine-2-yl]-5-trifluoromethyl-1H-pyrazole-4-carboxylate

Product 1

HCID 136356801Ethyl 1-[6-(2-hydroxy-3-iodophenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

To a suspension of the title compound from Example 5 Step B (4.0 g, 10.6 mmol) and silver sulfate (3.31 g, 10.6 mmol) in ethanol (20 mL) was added iodine (2.69 g, 10.6 mmol), and the resulting mixture was vigorously stirred at room temperature. After 2 h, the reaction mixture was quenched with water and sodium bisulfite solution, extracted with ethyl acetate and concentrated in vacuo. Purification by chromatography on silica gel (0 to 15% EtOAc in hexanes, then 15 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 503.7 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 13.08 (s, 1 H),8.17 (s, 1 H),8.10 (t, J=8.0 Hz, 1 H),8.06 (d, J=8.0 Hz, 1 H),7.86 (dd, J=7.5, 1.5 Hz, 1 H),7.82 (dd, J=8.0, 1.5 Hz, 1 H),7.52 (d, J=7.5 Hz, 1 H),6.75 (t, J=8.0 Hz, 1 H),4.33 (q, J=7.0 Hz, 2 H),1.43 (t, J=7.0 Hz, 3 H).

Workup

  1. customthe reaction mixture was quenched with water and sodium bisulfite solution
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. customPurification by chromatography on silica gel (0 to 15% EtOAc in hexanes

Sources & evidence

ORD record
ord-7b61031f9a654ce497ca5abba1cdc449
Source dataset
uspto-grants-2014_11
Patent number
US08895583B2

Linked notes

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