Water → [6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol

HRID 2279117Notes

Reaction equation

HRID 2279117 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[C:15]([CH3:16])=[N:14][N:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[C:8]=2[N:9]=[C:10]([Br:12])[CH:11]=1)=O)C.[BH4-].[Li+].O.C(OCC)(=O)C>C1COCC1>[Br:12][C:10]1[N:9]=[C:8]2[N:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[N:14]=[C:15]([CH3:16])[C:7]2=[C:6]([CH2:4][OH:3])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 866803196-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

Product 1

HCID 90014303[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanolYield 105.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 139 mg 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]-pyridine-4-carboxylic acid ethyl ester in 8 ml of dry THF was cooled to −20° C. and 18 mg of lithium borohydride was added. After 10 min at −20° C., the reaction was slowly brought to rt. After 1.5 h at rt water and ethyl acetate were added to the reaction. The phases were separated and the organic phase was dried over sodium sulphate, filtrated and concentrated in vacuo to obtain 130 mg (98%) of the title compound as a crude product, which was used without purification in the subsequent step.

Workup

  1. customwas slowly brought to rt
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15a7df36057c4b7da991245f2e32e5fd
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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