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

HRID 1255176

反応式

HRID 1255176 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-104d531e77e54f7ebcf9e7c536977096
出典データセット
uspto-grants-2013_06
特許番号
US08455638B2

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