Pyridine → 2-(3-{3-[2-benzyl-7-(trifluoromethyl)-2H-indazol-3-yl]phenoxy}phenyl)-2-methylpropanoic acid methyl ester

HRID 735482Notes

Reaction equation

HRID 735482 reaction equation
[CH2:1]([N:8]1[C:16]([C:17]2[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=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.[CH3:28][O:29][C:30](=[O:49])[C:31]([CH3:48])([C:33]1[CH:38]=[CH:37][CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=1)[CH3:32].N1C=CC=CC=1>C(Cl)Cl.Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:28][O:29][C:30](=[O:49])[C:31]([C:33]1[CH:34]=[CH:35][CH:36]=[C:37]([O:23][C:19]2[CH:20]=[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]=2)[CH:38]=1)([CH3:48])[CH3:32]

Participants

7

Reactant 3

HCID 1049PyridineHCID 116175953-(2-Benzyl-7-trifluoromethyl-2H-indazol-3-yl)-phenolHCID 67021194Methyl 2-methyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

Product 1

HCID 670213972-(3-{3-[2-benzyl-7-(trifluoromethyl)-2H-indazol-3-yl]phenoxy}phenyl)-2-methylpropanoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

3-(2-Benzyl-7-trifluoromethyl-2H-indazol-3-yl)-phenol (96 mg, 0.26 mmol), 2-methyl-2-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester (80 mg, 0.26 mmol), Cu(OAc)2 (47 mg, 0.26 mmol) and pyridine (42 μL, 0.52 mmol) were dissolved in 3 ml anhydrous CH2Cl2 and stirred at room temperature with crushed molsieves (4 Å) overnight. The reaction mixture was diluted with 1 M HCl (aq.) and the product was extracted three times with CH2Cl2. The combined organic phases were dried, evaporated and the crude material was purified by preparative HPLC using a gradient with an acidic mobile phase on an ACE-C8 column to afford 8.4 mg of analytically pure product.

Workup

  1. extractionthe product was extracted three times with CH2Cl2
  2. customThe combined organic phases were dried
  3. customevaporated
  4. customthe crude material was purified by preparative HPLC
  5. customto afford 8.4 mg of analytically pure product

Sources & evidence

ORD record
ord-8ee571b4d47b4a52a27a4e0cb0805b36
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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