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Potassium Carbonate → 6-(4-(Trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 406416
Notes
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Reaction equation

HRID 406416 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[CH:7]=1.[F:11][C:12]([F:24])([F:23])[O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:11][C:12]([F:23])([F:24])[O:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([CH:8]=[N:9][N:10]=3)[CH:7]=2)=[CH:16][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 177500186-Bromo-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 668494156-(4-(Trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridineYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

In a 5 mL vial 6-bromo-[1,2,4]triazolo[4,3-a]pyridine (93 mg), 4-trifluoromethoxyphenylboronic acid (115 mg), and potassium carbonate (187 mg) were suspended in DMF (2 mL) that was previously degassed with nitrogen. Tetrakis(triphenylphosphine) palladium (20 mg) was added and the reaction mixture was heated in a microwave reactor at 150° C. for 30 min, filtered, and concentrated. The residue was subjected to gradient chromatography (MeOH/dichloromethane) to produce white powder, 56.4 mg (43% yield).

Workup

  1. customwas previously degassed with nitrogen
  2. additionTetrakis(triphenylphosphine) palladium (20 mg) was added
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto produce white powder, 56.4 mg (43% yield)

Sources & evidence

ORD record
ord-63b205d7ebb84038b8dcb98c7d6a6e46
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08754103B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes