Cesium carbonate → 4-[4-(2-benzyl-7-trifluoromethyl-2H-indazol-3-yl)-phenoxy]-benzoic acid methyl ester

HRID 735408ノート

反応式

HRID 735408 の反応式
[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:24]([F:27])([F:26])[F:25])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:34][O:35][C:36](=[O:44])[C:37]1[CH:42]=[CH:41][C:40](Br)=[CH:39][CH:38]=1>N1C=CC=CC=1.Cl.[Cu]I>[CH3:34][O:35][C:36](=[O:44])[C:37]1[CH:42]=[CH:41][C:40]([O:23][C:20]2[CH:21]=[CH:22][C:17]([C:16]3[N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[N:9]=[C:10]4[C:15]=3[CH:14]=[CH:13][CH:12]=[C:11]4[C:24]([F:27])([F:25])[F:26])=[CH:18][CH:19]=2)=[CH:39][CH:38]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 12081Methyl 4-bromobenzoateHCID 136393280HCID 136393280、化合物

生成物 1

HCID 670211564-[4-(2-benzyl-7-trifluoromethyl-2H-indazol-3-yl)-phenoxy]-benzoic acid methyl ester

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 313Hydrochloric Acid溶媒HCID 1049Pyridine溶媒

実験手順

4-(2-Benzyl-7-trifluoromethyl-2H-indazol-3-yl)-phenol (180 mg, 0.5 mmol), cesium carbonate (490 mg, 1.5 mmol), CuI (20 mg, 0.1 mmol) and 4-bromo-benzoic acid methyl ester (215 mg, 1.0 mmol) were dissolved in 3 ml of dry pyridine. The reaction mixture was run in microwave (Emory's Optimizer, Personal Chemistry) at 200° C. for 30 min. After cooling to room temperature, the reaction mixture was diluted with 1 M HCl (aq.) and the product extracted three times with CH2Cl2. Combined organic phases were dried and evaporated, and the crude material was purified with preparative HPLC using a gradient with an acidic mobile phase on an ACE-C8 column to afford 151 mg of analytically pure product.

後処理

  1. extractionthe product extracted three times with CH2Cl2
  2. customCombined organic phases were dried
  3. customevaporated
  4. customthe crude material was purified with preparative HPLC
  5. customto afford 151 mg of analytically pure product

出典と根拠

ORDレコード
ord-493250861f1f4fccad2428562836a3ec
出典データセット
uspto-grants-2009_09
特許番号
US07592363B2

反応ノート

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