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

HRID 735408노트

반응식

HRID 735408 반응식
[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

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 12081Methyl 4-bromobenzoateHCID 136393280HCID 136393280, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 313Hydrochloric Acid용매HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-493250861f1f4fccad2428562836a3ec
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592363B2

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