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

HRID 735408Notes

Reaction equation

HRID 735408 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-493250861f1f4fccad2428562836a3ec
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

Loading…