Water → 1-Methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine

HRID 1854510Notes

Reaction equation

HRID 1854510 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]2=[C:9]3[CH:15]=[CH:14][NH:13][C:10]3=[N:11][CH:12]=[C:7]2[CH:6]=[N:5]1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>CN(C=O)C>[CH3:3][N:4]1[C:8]2=[C:9]3[CH:15]=[CH:14][N:13]([S:22]([C:19]4[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=4)(=[O:24])=[O:23])[C:10]3=[N:11][CH:12]=[C:7]2[CH:6]=[N:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 178481757HCID 178481757, compound

Product 1

HCID 580098301-Methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridineYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of NaH (60% dispersion in mineral oil, 0.209 g, 5.23 mmol) in DMF (10 mL) at about 0° C. was added a solution of 1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.60 g, 3.5 mmol) in DMF (5 mL). The cooling bath was removed and after about 20 min, p-toluenesulfonyl chloride (0.996 g, 5.23 mmol) was added. After about 2 h at room temperature, water was added (15 mL) and the mixture was extracted with EtOAc (3×20 mL). The organic layers were combined, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with a gradient of 5-45% EtOAc in heptane to give 1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.50 g, 44%): LC/MS (Table 2, Method d) Rt=2.20 min; MS m/z: 327 (M+H)+.

Workup

  1. customThe cooling bath was removed and after about 20 min
  2. extractionthe mixture was extracted with EtOAc (3×20 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a gradient of 5-45% EtOAc in heptane

Sources & evidence

ORD record
ord-eb48c607bc8f417e9ef7f6254ad64774
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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