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

HRID 354241
Notes
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Reaction equation

HRID 354241 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 962WaterHCID 129887472-[3-(3-fluorophenyl)-2H-azirin-2-yl]-5-trifluoromethylpyridine

Product 1

HCID 99217682-(3-Fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-A]pyridineYield 60.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

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

  1. temperatureThe reaction was cooled to room temperature
  2. stirringstirred for 30 min
  3. customThe solid was isolated by filtration
  4. custompartially dried via airflow
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes