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Pyridine → 5-Methyl-3-pyridin-4-yl-1-(3-trifluoromethoxy-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1011960
Notes
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Reaction equation

HRID 1011960 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:8][NH:9][C:10]=1[CH3:11])=[O:5])[CH3:2].[F:18][C:19]([F:31])([F:30])[O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)=[N:8][N:9]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([O:20][C:19]([F:18])([F:30])[F:31])[CH:22]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1049PyridineHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 67314713HCID 67314713, compound

Product 1

HCID 673149215-Methyl-3-pyridin-4-yl-1-(3-trifluoromethoxy-phenyl)-1H-pyrazole-4-carboxylic acid ethyl esterYield 54%

Reagents, catalysts & solvents 2

HCID 8895
Cupric acetate
Catalyst
HCID 6344DichloromethaneSolvent2×

Procedure

A blue-green suspension of 5-methyl-3-pyridin-4-yl-1H-pyrazole-4-carboxylic acid ethyl ester (700 mg, 3.03 mmol), molecular sieves 4A, 3-(trifluoromethoxy)benzeneboronic acid (1.25 g, 6.05 mmol), copper (II) acetate (824 mg, 4.54 mmol) and pyridine (0.48 ml, 6.05 mmol) in 14 ml CH2Cl2 was stirred under argon atmosphere and at room temperature for 5 days. The reaction mixture was diluted with CH2Cl2 and washed with a saturated solution of NaHCO3 and brine. The aqueous phases were extracted twice with CH2Cl2, the combined organic layers dried over magnesium sulfate, and evaporated. The residue was treated with EtOAc:toluene, 1:9, filtered off. The filtrate was evaporated and chromatographed twice (amino-phase silica gel, toluene:EtOAc 9:1) to afford the title compound as a colorless oil (638 mg, 54%). MS: 392.1 (MH+).

Workup

  1. washwashed with a saturated solution of NaHCO3 and brine
  2. extractionThe aqueous phases were extracted twice with CH2Cl2
  3. dry with materialthe combined organic layers dried over magnesium sulfate
  4. customevaporated
  5. additionThe residue was treated with EtOAc
  6. filtrationtoluene, 1:9, filtered off
  7. customThe filtrate was evaporated
  8. customchromatographed twice (amino-phase silica gel, toluene:EtOAc 9:1)

Sources & evidence

ORD record
ord-5fbeeaa50d7943b18e1436d15683eeee
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977358B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes