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

HRID 1627989Notes

Reaction equation

HRID 1627989 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.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].O>CN(C=O)C>[CH3:3][N:4]1[C:8]2=[C:9]3[CH:15]=[CH:14][N:13]([S:16]([C:19]4[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=4)(=[O:18])=[O:17])[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 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 60 wt % NaH (1.74 g, 43.6 mmol) in DMF (70 mL) at 0° C. was treated with a mixture of 1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (5.00 g, 29.0 mmol) in DMF (20 mL). After 20 min, TsCl (8.30 g, 43.6 mmol) was added. After 2 h, water (90 mL) was added and the precipitate formed was collected by filtration to give 1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (9.0 g, 95%): LC/MS (Table 2, Method c) Rt=1.44 min; MS m/z 327 (M+H)+

Workup

  1. waitAfter 2 h
  2. customthe precipitate formed
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-e1e42d9f3ed649ad956caf15812e6b3c
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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