Benyltrimethylammonium tetrachloroiodate → Ethyl 1-[6-(5-chloro-2-hydroxyphenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1255176

Reaction equation

HRID 1255176 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([Cl:31])(=O)=O.I(Cl)(=O)=O.I(Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>C(Cl)Cl>[Cl:31][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([C:8]2[N:13]=[C:12]([N:14]3[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]3)[CH:11]=[CH:10][CH:9]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 57347110Benyltrimethylammonium tetrachloroiodateHCID 136298134Ethyl 1-[6-(2-hydroxylphenyl)pyridine-2-yl]-5-trifluoromethyl-1H-pyrazole-4-carboxylate

Product 1

HCID 136356800Ethyl 1-[6-(5-chloro-2-hydroxyphenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound from Example 1 Step B (1.00 g, 2.65 mmol) in DCM (13 mL) was added benzyltrimethylammonium tetrachloroiodate (1.13 g, 2.70 mmol) and the resulting mixture was allowed to stir at ambient temperature. After 24 h, the mixture was concentrated in vacuo. Purification by chromatography on silica gel (0 to 18% EtOAc in hexanes, then 18 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 412.0 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 11.98 (s, 1H), 8.18 (s, 1H), 8.10 (t, J=8.0 Hz, 1H), 8.00 (d, J=8.0 Hz, 1H), 7.78 (br s, 1H), 7.55 (d, J=8.0 Hz, 1H), 7.30 (dd, J=9.0, 2.0 Hz, 1H), 6.98 (d, J=9.0 Hz, 1H), 4.39 (q, J=7.0 Hz, 2H), 1.40 (t, J=7.0 Hz, 3H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customPurification by chromatography on silica gel (0 to 18% EtOAc in hexanes

Sources & evidence

ORD record
ord-104d531e77e54f7ebcf9e7c536977096
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Linked notes

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