Pyridine → 6-Bromo-2,7-dimethyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine
Reaction equation
[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.CO[C:22](OC)([N:24](C)C)[CH3:23].N1C=CC=CC=1.NOS(O)(=O)=O>CN(C=O)C>[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[CH:10]=2)[C:5]2[N:6]([N:24]=[C:22]([CH3:23])[N:8]=2)[CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
To a stirred solution of 5-bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-ylamine (Int. 1, 1.0 g, 3.02 mmol) in DMF (5 mL) was added dimethylacetamide dimethyl acetal (1.33 mL, 9.06 mmol) and the reaction mixture was heated at 130° C. for 3 hrs. The reaction mixture was cooled then concentrated in vacuo. The resultant residue was dissolved in MeOH (10 mL) and pyridine (486 μL, 6.04 mmol) was added before the mixture was cooled to 0° C. and hydroxylamine-O-sulfonic acid (512 mg, 4.53 mmol) was added. The reaction mixture was allowed to warm to RT and stirred at this temperature for 20 hrs. The resultant precipitate was collected by filtration, then washed with MeOH to afford the title compound as a grey solid (323 mg).
Workup
- temperatureThe reaction mixture was cooled
- concentrationthen concentrated in vacuo
- dissolutionThe resultant residue was dissolved in MeOH (10 mL)
- temperaturewas cooled to 0° C.
- temperatureto warm to RT
- filtrationThe resultant precipitate was collected by filtration
- washwashed with MeOH
Sources & evidence
- ORD record
- ord-32883b72d4974a43b7719206b20b7947
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09199984B2
Reaction notes
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