Pyridine → N-(2-Phenyl-2H-pyrazolo[3,4-b]pyridin-5-yl)benzenesulfonamide

HRID 901216Notes

Reaction equation

HRID 901216 reaction equation
[C:1]1([N:7]2[CH:15]=[C:14]3[C:9]([N:10]=[CH:11][C:12]([NH2:16])=[CH:13]3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC#N>[C:1]1([N:7]2[CH:15]=[C:14]3[C:9]([N:10]=[CH:11][C:12]([NH:16][S:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)(=[O:31])=[O:30])=[CH:13]3)=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 586701512-Phenyl-2H-pyrazolo[3,4-b]pyridin-5-amine

Product 1

HCID 58670149N-(2-Phenyl-2H-pyrazolo[3,4-b]pyridin-5-yl)benzenesulfonamideYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3C (305 mg, 1.458 mmol) and pyridine (0.7 mL) in CH3CN (30 mL) cooled to 0° C. was added bezenesulfonyl chloride (274 mg, 1.550 mmol). After addition, the reaction mixture was stirred at RT for 1 hour, then concentrated under reduced pressure. The resultant residue was dissolved in CH2Cl2 (100 mL), washed with water (2×50 mL), saturated NaCl (50 mL). The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified by silica gel column chromatography eluting with 2% of 2 M NH3 in MeOH/CH2Cl2 to give the title compound as a light brown solid (200 mg, 40% yield). LC/MS (method A): retention time=2.78 min, (M+H)+=351.

Workup

  1. additionAfter addition
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resultant residue was dissolved in CH2Cl2 (100 mL)
  4. washwashed with water (2×50 mL), saturated NaCl (50 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with 2% of 2 M NH3 in MeOH/CH2Cl2

Sources & evidence

ORD record
ord-549e6d1a5b5b4d3090466275936c62f1
Source dataset
uspto-grants-2008_04
Patent number
US07361766B2

Reaction notes

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