Potassium Carbonate → HCID 66587467, compound

HRID 1630682Notes

Reaction equation

HRID 1630682 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1.Cl[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=1.C1(P(C2CCCCC2)C2(C(C)C)CC(C(C)C)=CC(C(C)C)=C2C2C=CC=CC=2)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C.O>[Cl:17][C:16]1[C:11]([N:4]2[C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:6][C:2]([NH:1][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=3)=[N:3]2)=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 66587433HCID 66587433, compoundHCID 672859322-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl

Product 1

HCID 66587467HCID 66587467, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

1.90 g (7.52 mmol) of methyl 3-amino-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate 1.50 g (8.27 mmol) of 2-chloro-5-trifluoromethylpyridine, 0.275 g (0.3 mmol) of tris(dibenzylacetone)dipalladium, 0.286 g (0.60 mmol) of 2-dicyclohexylphosphino-2,4,6-triisopropyl-1,1-biphenyl and 3.12 g (22.5 mmol) of potassium carbonate were initially charged in 190 ml of tert-butanol, and the reaction mixture was stirred at 100° C. for 24 hours. After cooling, the mixture was poured into water and extracted repeatedly with ethyl acetate, and the extracts were dried over magnesium sulphate. The solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel, which gave 950 mg (29% of theory) of methyl 1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)pyridin-2-yl]amino}-1H-pyrazole-5-carboxylate. (logP: 3.14; MH+: 398.0); 1H-NMR (400 MHz, CD3CN, δ, ppm): 3.74 (s, 3H), 7.26 (m, 1H), 7.37 (s, 1H), 7.66 (m, 1H), 7.95 (m, 1H), 8.25 (d, 1H), 8.56 (m, 2H).)

Workup

  1. temperatureAfter cooling
  2. extractionextracted repeatedly with ethyl acetate
  3. dry with materialthe extracts were dried over magnesium sulphate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was chromatographed on silica gel, which

Sources & evidence

ORD record
ord-8f649d2ce9ff41248de04320bc5632c2
Source dataset
uspto-grants-2014_07
Patent number
US08791139B2

Reaction notes

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