Sodium Bicarbonate → HCID 69671539, compound

HRID 1497568Notes

Reaction equation

HRID 1497568 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])=[N:19][N:20]=3)[CH:17]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.C([O-])(O)=O.[Na+]>CO>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])=[N:19][N:20]=3)[CH:17]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69670952HCID 69670952, compound

Product 1

HCID 69671539HCID 69671539, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A flask was charged with 6-(3-methoxy-4-nitrophenyl)-3-(2-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine (100 mg, 0.27 mmol), stannous chloride dihydrate (SnCl2, 300 mg, 1.35 mmol) and MeOH (10 mL). The mixture was stirred at 50° C. under Argon for 4 h. The pH of the mixture was adjusted to around 9 by progressively adding solid NaHCO3, and it was evaporated to afford the crude product. The crude product was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=1:1) to give the title compound (28.5 mg, 31.2% yield) as yellow solids. 1H NMR (DMSO-d6): 7.99 (s, 1H), 7.87 (d, J=9.6 Hz, 1H), 7.75 (d, J=9.6 Hz, 1H), 7.67-7.61 (m, 2H), 7.32 (d, J=8.4 Hz, 1H), 7.19 (t, J=7.5 Hz, 1H), 7.07 (d, J=1.8 Hz, 1H), 7.02 (dd, J=8.1 and 1.8 Hz, 1H), 6.71 (d, J=8.1 Hz, 1H), 5.00 (s, 2H), 3.89 (s, 3H), 3.85 (s, 3H). MS: m/z 347.2 [M+H+].

Workup

  1. customwas evaporated
  2. customto afford the crude product
  3. customThe crude product was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-13248db5e565417090f230ea64c4849c
Source dataset
uspto-grants-2015_12
Patent number
US09199983B2

Reaction notes

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