Water → 2-(3-Fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-A]pyridine

HRID 354241Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.O>COCCOC>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 2-[3-(3-fluorophenyl)-2H-azirin-2-yl]-5-trifluoromethylpyridine (2.2 g, 7.85 mmol) in DME (10 ml) was added FeCl2 (10 mg, 0.079 mmol). The solution was warmed to 75° C. and stirred for 2 hours. The reaction was cooled to room temperature and added to H2O (180 ml). The resultant suspension was cooled to 0° C. and stirred for 30 min. The solid was isolated by filtration and partially dried via airflow. Recrystallization of the crude product in IPA afforded 1.34 g (60%) of the title compound as an off-white solid.

Workup

temperatureThe reaction was cooled to room temperature
stirringstirred for 30 min
customThe solid was isolated by filtration
custompartially dried via airflow
customRecrystallization of the crude product in IPA

Sources & evidence

ORD record: ord-384f035b4c4f4805be1a1a8ffb068f6b
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06756498B2

Reaction notes

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