Potassium Phosphate, Tribasic → Tert-butyl 8-(4-fluorophenyl)-3-pyridin-2-yl[1,2,4]triazolo[4,3-a]pyridine-6-carboxylate

HRID 592301Notes

Reaction equation

Cl[C:2]1[C:3]2[N:4]([C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:16][N:17]=2)[CH:5]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:7]=1.[F:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[C:3]3[N:4]([C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[N:16][N:17]=3)[CH:5]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:7]=2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of tert-butyl 8-chloro-3-pyridin-2-yl[1,2,4]triazolo[4,3-a]pyridine-6-carboxylate (0.5 g, 1.51 mmol) in toluene (12 mL) were added (4-fluorophenyl)boronic acid (0.32 g, 2.27 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (72.1 mg, 0.15 mmol), palladium(II) acetate (33.9 mg, 0.15 mmol) and potassium phosphate tribasic (0.96 g, 4.53 mmol). The mixture was heated to 110° C. After 2 h, the mixture was cooled to ambient temperature, filtered with Celite and the filtrate was concentrated. Purification by silica gel chromatography (100% dichloromethane→60% dichloromethane/ethyl acetate) gave of the title compound (0.53 g): LC-MS [M+1]=391.2.

Workup

temperaturethe mixture was cooled to ambient temperature
filtrationfiltered with Celite
concentrationthe filtrate was concentrated
customPurification by silica gel chromatography (100% dichloromethane→60% dichloromethane/ethyl acetate)

Sources & evidence

ORD record: ord-e6a1d6a5c0d145e2a5a35a01244c3a43
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238647B2

Reaction notes

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