Sodium Carbonate → 8-(2-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

HRID 472255Notes

Reaction equation

HRID 472255 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[C:22]2[N:23]([N:27]=[C:28]([NH2:30])[N:29]=2)[CH:24]=[CH:25][CH:26]=1.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[CH3:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:21]1[C:22]2[N:23]([N:27]=[C:28]([NH2:30])[N:29]=2)[CH:24]=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27339582-Methoxyphenylboronic acidHCID 468640698-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine

Product 1

HCID 575023708-(2-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

An oven dried tube was charged with palladium acetate (0.20 g, 0.89 mmol) and triphenylphosphine (0.60 g, 2.3 mmol). The tube was evacuated under high vacuum and backflushed under a stream of nitrogen for 5 minutes. 1,4-Dioxane (10 mL) was added and the mixture was stirred under nitrogen for 10 minutes. 8-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (1.0 g, 4.7 mmol), 2-methoxybenzeneboronic acid (1.1 g, 7.0 mmol), N,N-dimethylformamide (10 mL) and 1.50 M of sodium carbonate in water (10 mL) were added. The mixture was stirred for 2 minutes at room temperature under nitrogen then the tube was sealed and heated at 80° C. for 18 hours. The mixture was transferred to a round bottom flask and the volatiles were evaporated under reduced pressure. Water (100 mL) was added and the mixture was stirred when a precipitate was formed. The solid was collected by filtration, rinsed with water, air dried, triturated with ether/dichloromethane (4:1; 10 mL), filtered and rinsed with ether. 8-(2-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was isolated (1.0 g, 89%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.50 (d, J=6.5 Hz, 1H), 7.51 (dd, J=7.6, 1.5 Hz, 1H), 7.43-7.36 (m, 2H), 7.13 (d, J=8.1 Hz, 1H), 7.02 (t, J=7.3 Hz, 1H), 6.91 (t, J=7.0 Hz, 1H), 5.96 (br s, 2H), 3.73 (s, 3H). MS=241 (MH)+.

Workup

  1. customAn oven dried tube
  2. customThe tube was evacuated under high vacuum
  3. addition1,4-Dioxane (10 mL) was added
  4. stirringThe mixture was stirred for 2 minutes at room temperature under nitrogen
  5. customthe tube was sealed
  6. customThe mixture was transferred to a round bottom flask
  7. customthe volatiles were evaporated under reduced pressure
  8. additionWater (100 mL) was added
  9. stirringthe mixture was stirred when a precipitate
  10. customwas formed
  11. filtrationThe solid was collected by filtration
  12. washrinsed with water, air
  13. customdried
  14. customtriturated with ether/dichloromethane (4:1; 10 mL)
  15. filtrationfiltered
  16. washrinsed with ether

Sources & evidence

ORD record
ord-13935cdae5f4414bbc53f3b8633b1be6
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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