Sodium Carbonate → 8-(3,4-Difluorophenyl)-[1,2,4]triazolo[1,5-A]pyridin-2-amine

HRID 2368035Notes

Reaction equation

HRID 2368035 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:18]=1[F:19].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[F:12][C:13]1[CH:14]=[C:15]([C:2]2[C:3]3[N:4]([N:8]=[C:9]([NH2:11])[N:10]=3)[CH:5]=[CH:6][CH:7]=2)[CH:16]=[CH:17][C:18]=1[F:19]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343373,4-Difluorobenzeneboronic acidHCID 468640698-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine

Product 1

HCID 673372048-(3,4-Difluorophenyl)-[1,2,4]triazolo[1,5-A]pyridin-2-amineYield 102.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (5.33 g, 25 mmol), 3,4-difluorophenylboronic acid (5.92 g, 37.5 mmol) and 2M aqueous sodium carbonate solution (62.5 mL, 125 mmol) in 1,4-dioxane (250 mL) was treated with 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (1.02 g, 1.25 mmol) at room temperature and then stirred for 18 hours at 110° C. The reaction was cooled to room temperature and separated between water (312 mL) and ethyl acetate (500 mL). The aqueous layer was extracted with further ethyl acetate (500 mL). The organic layers were washed with saturated aqueous sodium chloride solution (300 mL), combined, dried over sodium sulfate, filtered off and evaporated. The brown solid was trituration with diethyl ether (130 mL) and dichloromethane (25 mL) to yield the title compound as a light brown solid (6.33 g, 97%). MS ISP (m/e): 247.2 (100) [(M+H)+].

Workup

  1. additionwas treated with 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (1.02 g, 1.25 mmol) at room temperature
  2. temperatureThe reaction was cooled to room temperature
  3. customseparated between water (312 mL) and ethyl acetate (500 mL)
  4. extractionThe aqueous layer was extracted with further ethyl acetate (500 mL)
  5. washThe organic layers were washed with saturated aqueous sodium chloride solution (300 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered off
  8. customevaporated

Sources & evidence

ORD record
ord-646f25aa273a445a8c587878b33c74c6
Source dataset
uspto-grants-2014_04
Patent number
US08703763B2

Reaction notes

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