Potassium Carbonate → 6-(4-Cyclopropylphenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 406417

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=2)[CH:7]=1.[CH:15]1([C:18]2[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:15]1([C:18]2[CH:23]=[CH:22][C:21]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=4)[CH:7]=3)=[CH:20][CH:19]=2)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 6-bromo-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine (50 mg, 0.19 mmol), 4-cyclopropyl phenylboronic acid (34 mg, 0.21 mmol), dppf(Pd)Cl2 (6.9 mg, 0.094 mmol), potassium carbonate (52 mg, 0.62 mmol) in degassed toluene (1 mL), degassed water (0.5 mL) and degassed ethanol (0.5 mL) was heated at 90° C. for 1 hour. The layers are separated, the organic layer was concentrated and the residue was purified by column chromatography to provide 6-(4-cyclopropylphenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine as a white powder.

Workup

customdegassed water (0.5 mL)
customdegassed ethanol (0.5 mL)
customThe layers are separated
concentrationthe organic layer was concentrated
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-919e50792a8544b68a08805ddfb0ac2f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754103B2

Linked notes

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