Sodium borohydride → {5-(bromomethyl)-3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydroisoxazol-5-yl}methanol

HRID 1966826Notes

Reaction equation

HRID 1966826 reaction equation
[Br:1][CH2:2][C:3]1([C:26](OCC)=[O:27])[O:7][N:6]=[C:5]([C:8]2[C:9]([NH:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:10]3[CH:16]=[N:15][N:14]([CH2:17][CH3:18])[C:11]3=[N:12][CH:13]=2)[CH2:4]1.[BH4-].[Na+]>O1CCCC1>[Br:1][CH2:2][C:3]1([CH2:26][OH:27])[O:7][N:6]=[C:5]([C:8]2[C:9]([NH:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)=[C:10]3[CH:16]=[N:15][N:14]([CH2:17][CH3:18])[C:11]3=[N:12][CH:13]=2)[CH2:4]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66732635ethyl 5-(bromomethyl)-3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydroisoxazole-5-carboxylate

Product 1

HCID 66733284{5-(bromomethyl)-3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydroisoxazol-5-yl}methanolYield 65.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-(bromomethyl)-3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydroisoxazole-5-carboxylate (200 mg, 0.0004 mole) (example 19) was taken in tetrahydrofuran (15 ml). Sodium borohydride (31 mg, 0.0008 mole) was added portion wise. The reaction mixture was stirred overnight. It was quenched with saturated ammonium chloride solution. The organic solvent was removed, water was added and the mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product obtained was purified by column chromatography.

Workup

  1. customIt was quenched with saturated ammonium chloride solution
  2. customThe organic solvent was removed
  3. additionwater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-254d24d8621147389eb4113bd0c9e813
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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