Sodium ethoxide → 8-(3,4-Difluorophenyl)-N-(1-(2-ethoxypyridin-4-yl)piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 451508Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[N:31]=[C:18]4[C:19]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=5)=[CH:20][CH:21]=[CH:22][N:17]4[N:16]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[O-:32][CH2:33][CH3:34].[Na+]>CCO>[F:30][C:25]1[CH:24]=[C:23]([C:19]2[C:18]3[N:17]([N:16]=[C:15]([NH:14][CH:11]4[CH2:12][CH2:13][N:8]([C:6]5[CH:5]=[CH:4][N:3]=[C:2]([O:32][CH2:33][CH3:34])[CH:7]=5)[CH2:9][CH2:10]4)[N:31]=3)[CH:22]=[CH:21][CH:20]=2)[CH:28]=[CH:27][C:26]=1[F:29]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of N-(1-(2-chloropyridin-4-yl)piperidin-4-yl)-8-(3,4-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (example 169c) (88 mg, 0.20 mmol) in EtOH (1 mL) was added sodium ethoxide solution (21% in ethanol, 75 L, 0.2 mmol) and the reaction mixture was heated in the microwave to 150° C. for 30 minutes. Again sodium ethoxide solution (21% in ethanol, 75 L, 0.2 mmol) was added and the resulting mixture heated to 150° C. for another 30 minutes. The mixture was then evaporated. Purification by chromatography (silica gel, 20 g, 0 to 100% methanol in dichloromethane) afforded the title compound (3 mg, 3%) as a colourless gum.

Workup

temperaturethe resulting mixture heated to 150° C. for another 30 minutes
customThe mixture was then evaporated
customPurification by chromatography (silica gel, 20 g, 0 to 100% methanol in dichloromethane)

Sources & evidence

ORD record: ord-68bec01d877248b4b43ff3f35c697a2b
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

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