HCID 178428388, compound → 6-Fluoro-2-(4-methyl-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 717552Notes

Reaction equation

HRID 717552 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[NH:17])[C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[N:12][CH:11]=2)=[N:6][CH:7]=1>C1(C)C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:17]=[C:9]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][C:15]=3[CH3:16])[N:8]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 178428388HCID 178428388, compound

Product 1

HCID 894722946-Fluoro-2-(4-methyl-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

Lead tetra acetate (0.0693 g, 0.000156 mol) was added to a solution of N-(5-fluoro-pyridin-2-yl)-4-methyl-nicotinamidine (22-1; 0.360 g, crude 0.000156 mol) in toluene (10 mL) in a 40 mL microwave vial at RT. The reaction mixture heated to 150° C. for 1.5 h under microwave irradiation. The reaction mixture cooled to RT, diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was purified by silica gel column chromatography to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.40-9.38 (t, J=8 Hz, 1H), 9.12 (s, 1H), 8.51-8.50 (d, J=4 Hz, 1H), 8.00-7.97 (m, J=12 Hz, 1H), 7.75-7.80 (t, J=20 Hz, 1H), 7.40-7.39 (d, J=4 Hz, 1H), 2.68 (s, 3H). MS (M+1): 229.1.

Workup

  1. customat RT
  2. temperatureThe reaction mixture cooled to RT
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. concentrationconcentrated under vacuum
  6. customto afford the crude product, which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bbcd9cfd93e841ba8c66e2453cddbbd6
Source dataset
uspto-grants-2015_11
Patent number
US09193724B2

Reaction notes

Loading…