Potassium Carbonate → 2-[2-(2-Fluoro-ethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine

HRID 1802275Notes

Reaction equation

HRID 1802275 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[OH:17])[N:10]=[C:4]2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[F:24][CH2:25][CH2:26]Br>CN(C=O)C.O>[F:24][CH2:25][CH2:26][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]1[N:10]=[C:4]2[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][N:5]2[N:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 1363723582-(7-Amino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-phenol

Product 1

HCID 866660272-[2-(2-Fluoro-ethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-7-ylamineYield 111.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-(7-amino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-phenol (250 mg, 1.10 mmol) in dry DMF (6 ml), K2CO3 (611 mg, 4.42 mmol) was added under positive nitrogen pressure and the mixture was stirred for 20 min at rt in a sealed tube. A solution of 1-fluoro-2-bromoethane (93 mg, 0.66 mmol) in DMF was added dropwise and the reaction mixture was heated for 8 h at 90° C. On completion of reaction (monitored by TLC), the mixture was cooled, diluted with water and extracted with DCM. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to get the crude product. Purification by silica gel column chromatography using 2% MeOH in DCM as eluent afforded the desired product (200 mg, 66%) as off-white solid. LC-MS: m/z=273.2 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated for 8 h at 90° C
  2. customOn completion of reaction (monitored by TLC)
  3. temperaturethe mixture was cooled
  4. extractionextracted with DCM
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto get the crude product
  8. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-339584d0556b4130984ab0653fdd5d87
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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