Sodium methanesulfinate → HCID 59592702, compound

HRID 2261013Notes

Reaction equation

HRID 2261013 reaction equation
Br[CH2:2][C:3]1[N:8]=[C:7]2[N:9]([CH3:12])[N:10]=[CH:11][C:6]2=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH:4]=1.[CH3:22][S:23]([O-:25])=[O:24].[Na+]>CCO.CN(C=O)C>[CH3:22][S:23]([CH2:2][C:3]1[N:8]=[C:7]2[N:9]([CH3:12])[N:10]=[CH:11][C:6]2=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH:4]=1)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 59592674HCID 59592674, compound2×

Product 1

HCID 59592702HCID 59592702, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 19794673N,N-dimethylformamide ethanolSolvent

Procedure

1.04 g 6-bromomethyl-1-methyl-4-(4-nitro-phenyl)-1H-pyrazolo[3,4-b]pyridine (Intermediate 13.1; 3 mmol, 1 eq.) were dissolved in 55 mL 10:1 EtOH/DMF, treated with 459 mg sodium methanesulfinate (4.5 mmol, 1.5 eq.) and refluxed for 150 min. The mixture was cooled to rt and concentrated in vacuo. Addition of water was followed by precipitation to yield 1040 mg of the crude product (quantitative yield).

Workup

  1. temperaturerefluxed for 150 min
  2. concentrationconcentrated in vacuo
  3. additionAddition of water
  4. customwas followed by precipitation

Sources & evidence

ORD record
ord-ef9a795cb73d43808b89f6cc24795336
Source dataset
uspto-grants-2010_12
Patent number
US07846928B2

Reaction notes

Loading…