Sodium Methoxide → HCID 69671179, compound

HRID 1497580Notes

Reaction equation

HRID 1497580 reaction equation
Cl[C:2]1[C:7]([C:8]2[N:12]3[CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[CH:15]=[CH:16][C:11]3=[N:10][N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:25][O-:26].[Na+]>CO>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]2[CH:15]=[CH:16][C:11]3[N:12]([C:8]([C:7]4[C:2]([O:26][CH3:25])=[N:3][CH:4]=[CH:5][CH:6]=4)=[N:9][N:10]=3)[CH:13]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 87944273HCID 87944273, compound

Product 1

HCID 69671179HCID 69671179, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(2-chloropyridin-3-yl)-6-(4-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine (178 mg, 0.53 mmol) and sodium methoxide (518 mg, 9.6 mmol) in methanol (60 mL) was heated to reflux for 16 h under Argon. The reaction mixture was cooled to room temperature and concentrated. The residue was mixed with DCM (60 mL) and water (60 mL), and it was separated and the organic layer was washed with brine (50 mL×2) and concentrated. The residue was stirred at room temperature for 0.5 h in petroleum ether (35 mL) and ethyl acetate (5 mL) and filtered. The solids were dried in vacuo to give the title compound (150 mg, 84.0% yield). 1H NMR (DMSO-d6): 8.47 (dd, J=4.8 and 1.8 Hz, 1H), 8.32 (m, 1H), 8.10 (dd, J=7.2 and 1.8 Hz, 1H), 7.94 (dd, J=9.6 and 0.9 Hz, 1H), 7.79 (dd, J=9.6 and 1.5 Hz, 1H), 7.69 (d, J=8.7 Hz, 2H), 7.27 (dd, J=7.5 and 5.1 Hz, 1H), 7.05 (d, J=9.0 Hz, 2H), 3.95 (s, 3H), 3.80 (s, 3H). MS: m/z 333.2 [M+H+].

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h under Argon
  3. concentrationconcentrated
  4. additionThe residue was mixed with DCM (60 mL) and water (60 mL), and it
  5. customwas separated
  6. washthe organic layer was washed with brine (50 mL×2)
  7. concentrationconcentrated
  8. filtrationethyl acetate (5 mL) and filtered
  9. customThe solids were dried in vacuo

Sources & evidence

ORD record
ord-e24b749f569a428fbb9bc917662051a5
Source dataset
uspto-grants-2015_12
Patent number
US09199983B2

Reaction notes

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