Cesium carbonate → Tert-butyl 4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoate

HRID 240586Notes

Reaction equation

[Cl:1][C:2]1[C:3]([F:16])=[C:4]([CH:12]=[CH:13][C:14]=1F)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[N:17]1[CH:18]=[N:19][N:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]=12.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N:17]1[CH:18]=[N:19][N:20]2[CH:25]=[CH:24][C:23]([O:26][C:14]3[CH:13]=[CH:12][C:4]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])=[C:3]([F:16])[C:2]=3[Cl:1])=[CH:22][C:21]=12

Participants

Conditions

Temperature: 80 °C

Procedure

A vial charged with tert-butyl 3-chloro-2,4-difluorobenzoate (0.210 g, 0.845 mmol), [1,2,4]triazolo[1,5-a]pyridin-7-ol (0.114 g, 0.845 mmol), cesium carbonate (0.413 g, 1.27 mmol), and DMF (1.7 ml). The reaction was heated to 80° C. for 12 hours, then poured into ice water. The resulting solids were collected by filtration and purified by flash chromatography, eluting with gradient of 10% EtOAc/Hexanes to 50% EtOAc/Hexanes to provide the desired product.

Workup

filtrationThe resulting solids were collected by filtration
custompurified by flash chromatography
washeluting with gradient of 10% EtOAc/Hexanes to 50% EtOAc/Hexanes

Sources & evidence

ORD record: ord-ce0454587d364833bfaf0cd5daef20a3
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648087B2

Reaction notes

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