Trimethyl orthoformate → 2-(2-(Trifluoromethoxy)-5-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)phenyl)-1,3,4-oxadiazole
Reaction equation
[CH2:1]([O:3][C:4](=O)[C:5]1[CH:10]=[C:9](Br)[CH:8]=[CH:7][C:6]=1[O:12][C:13]([F:16])([F:15])[F:14])C.O.[NH2:19][NH2:20].COC(OC)OC.[F:28][C:29]([F:43])([F:42])[C:30]1[N:34]2[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][C:33]2=[N:32][N:31]=1>C(O)C>[F:14][C:13]([F:16])([F:15])[O:12][C:6]1[CH:7]=[CH:8][C:9]([C:36]2[CH:37]=[CH:38][C:33]3[N:34]([C:30]([C:29]([F:43])([F:42])[F:28])=[N:31][N:32]=3)[CH:35]=2)=[CH:10][C:5]=1[C:4]1[O:3][CH:1]=[N:19][N:20]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a round bottom flask was added ethyl-5-bromo-2-(trifluoromethoxy)benzoate (0.638 mmole) in ethanol (10 mL). To this solution was added 1 mL of hydrazine monohydrate and the resulting mixture was refluxed overnight. The reaction mixture was evaporated in vacuo to give A. To A was added trimethylorthoformate in a heavy wall pressure tube. This resulting mixture was heated at 100 C for 18 hours. The reaction mixture was concentrated down and purified by preparative TLC to afford B which was coupled with 3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-ylboronic acid using methods disclosed above to give 2-(2-(trifluoromethoxy)-5-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)phenyl)-1,3,4-oxadiazole.
Workup
- temperaturethe resulting mixture was refluxed overnight
- customThe reaction mixture was evaporated in vacuo
- customto give A
- temperatureThis resulting mixture was heated at 100 C for 18 hours
- concentrationThe reaction mixture was concentrated down
- custompurified by preparative TLC
- customto afford B which
Sources & evidence
- ORD record
- ord-2446a601984e40e08b9fc71e2499ceff
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754103B2
Reaction notes
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