Trifluoroacetic acid → 6-Bromo-8-phenyl-[1,2,4]triazolo[4,3-a]pyridine

HRID 2197540Notes

Reaction equation

HRID 2197540 reaction equation
C(OC)(OC)OC.[Br:8][C:9]1[CH:10]=[C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([NH:15][NH2:16])=[N:13][CH:14]=1.[C:23](O)(C(F)(F)F)=O>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]2[N:13]([CH:23]=[N:16][N:15]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9005Trimethyl orthoformateHCID 582078941-(5-Bromo-3-phenylpyridin-2-yl)hydrazine

Product 1

HCID 582079196-Bromo-8-phenyl-[1,2,4]triazolo[4,3-a]pyridineYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethyl orthoformate (564 μL, 5.16 mmol) was added into a solution of 1-(5-bromo-3-phenylpyridin-2-yl)hydrazine (1.29 mmol, crude) in CH2Cl2 (12 mL). TFA (100 μL, 1.29 mmol) was added after 15 mins. The reaction mixture was stirred at room temperature for 30 mins and then concentrated. The residue was purified by a flash column using a gradient of ethyl acetate (50-80%) in heptane as an eluent. The product containing fractions were concentrated to give 6-bromo-8-phenyl-[1,2,4]triazolo[4,3-a]pyridine (328.7 mg, 85% yield).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by a flash column
  3. additionThe product containing fractions
  4. concentrationwere concentrated

Sources & evidence

ORD record
ord-3ce77d18422f4493aee2fa781fc467f1
Source dataset
uspto-grants-2012_12
Patent number
US08338604B2

Reaction notes

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