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

HRID 1958464Notes

Reaction equation

HRID 1958464 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-acb779033c8e4b3f868bd98fe4a50d58
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

Loading…