Ethanamine, 2,2,2-trifluoro- → N-(2,2,2-Trifluoroethyl)-6-[1-methyl-3-(trifluoromethyl)pyrazol-5-yloxy]pyridine-2-carboxamide

HRID 650238Notes

Reaction equation

HRID 650238 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[N:3]=1.[F:19][C:20]([F:24])([F:23])[CH2:21][NH2:22].[C:25](=O)([O-])[O-:26].[Na+].[Na+].COC1C=CC(P(C2C=CC(OC)=CC=2)C2C=CC(OC)=CC=2)=CC=1>CC1CCCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:19][C:20]([F:24])([F:23])[CH2:21][NH:22][C:25]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[N:3]=1)=[O:26]

Participants

7

Reactant 4

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 10340Sodium CarbonateHCID 70071Phosphine, tris(4-methoxyphenyl)-HCID 217146352-Chloro-6-[1-methyl-3-(trifluoromethyl)pyrazol-5-yloxy]pyridine

Product 1

HCID 21714641N-(2,2,2-Trifluoroethyl)-6-[1-methyl-3-(trifluoromethyl)pyrazol-5-yloxy]pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7962MethylcyclohexaneSolvent2×

Procedure

Analogously to Example 14, 1.39 g (5 mmol) of 2-chloro-6-[1-methyl-3-(trifluoromethyl)-pyrazol-5-yloxy]pyridine, 0.75 g (7.57 mmol, 98 percent content) of 2,2,2-trifluoroethylamine, 0.80 g (7.55 mmol) of anhydrous sodium carbonate, 5.6 mg (25 μmol) of palladium(II) acetate and 88 mg (0.25 mmol) of tris(4-methoxyphenyl)phosphine in 20 ml of methylcyclohexane were reacted under a CO pressure of 21 bar. The yield was 0.96 g (75.4 percent) of a white solid. The melting point was 135.8° to 136.3° C. (from methylcyclohexane). Other data concerning the product was:

Sources & evidence

ORD record
ord-4b188bc1ef69481fbcb3b4e15ff580a4
Source dataset
uspto-grants-2001_08
Patent number
US06271372B1

Reaction notes

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