Methanesulfonyl chloride → Methanesulfonic acid 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl ester

HRID 2279118Notes

Reaction equation

HRID 2279118 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:9]=[C:10]([CH3:11])[C:5]2=[C:4]([CH2:18][OH:19])[CH:3]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:9]=[C:10]([CH3:11])[C:5]2=[C:4]([CH2:18][O:19][S:21]([CH3:20])(=[O:23])=[O:22])[CH:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 90014303[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol

Product 1

HCID 90013581Methanesulfonic acid 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl esterYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solutuion of 130 mg [6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol in 5 ml of dry DCM at 0° C. 77 μl of TEA were added, after 10 min followed by the addition of 60 mg of methanesulfonyl chloride. After 20 min at 0° C. the reaction was brought to rt and extracted with sat. aqueous ammonium chloride solution. The organic layer was separated, dried over sodium sulphate and freeze-dried to obtain 138 mg (85%) of the title compound as a crude product, which was used without purification in the subsequent step.

Workup

  1. customat 0° C
  2. extractionextracted with sat. aqueous ammonium chloride solution
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. customfreeze-dried

Sources & evidence

ORD record
ord-aa6f2054ff514e718ab255992a41895e
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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