Dimethyl Sulfate → 7-(2,4-dichloro-phenyl)-2-methyl-2H-pyrazolo[3,4-c]pyridine

HRID 902543Notes

Reaction equation

HRID 902543 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[N:16][NH:15][C:14]=12.[H-].[Na+].S(OC)(O[CH3:24])(=O)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]2=[N:15][N:16]([CH3:24])[CH:17]=[C:13]2[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydride2×HCID 686152427-(2,4-dichloro-phenyl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 597023037-(2,4-dichloro-phenyl)-2-methyl-2H-pyrazolo[3,4-c]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-(2,4-dichloro-phenyl)-1H-pyrazolo[3,4-c]pyridine (31; 0.107 g; 0.405 mmol), 4 mL of THF, and 60% sodium hydride/mineral oil (0.020 g, 0.50 mmol sodium hydride) was stirred for 3 h. To the green solution was added dimethyl sulfate (0.040 mL, 0.42 mmol). The resulting yellow, cloudy solution was stirred for 30 m, then quenched with silica gel and concentrated. Column chromatography (0→50% EtOAc/hexanes) afforded of 7-(2,4-dichloro-phenyl)-2-methyl-2H-pyrazolo[3,4-c]pyridine as a white solid (32; 0.029 g; 26%).

Workup

  1. stirringThe resulting yellow, cloudy solution was stirred for 30 m
  2. customquenched with silica gel
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-988bccd269be4888931d6c1feab5602d
Source dataset
uspto-grants-2008_04
Patent number
US07365211B2

Reaction notes

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