Sodium Hydroxide → HCID 178510688, compound

HRID 42585Notes

Reaction equation

HRID 42585 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:19]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:18]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[N:17]=[C:16]3[NH:33][N:34]=[C:35]([C:36]#[N:37])[C:15]=23)=[CH:10][CH:9]=1.[OH-].[Na+]>C(OCC)C.O.C1COCC1>[NH2:37][CH2:36][C:35]1[C:15]2[C:16](=[N:17][C:18]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[C:19]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[C:14]=2[C:11]2[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=2)[NH:33][N:34]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178510687HCID 178510687, compound

Product 1

HCID 178510688HCID 178510688, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

LiAlH4 (0.06 g, 1.5 mmol) and anhydrous diethyl ether (2 mL) were introduced into a volumetric flask. The mixture was cooled with an ice bath and a solution of 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile (0.15 g, 0.4 mmol, obtained in example 65) in diethyl ether (1 mL) was added dropwise. THF (2 mL) was added and the mixture was stirred at room temperature overnight. It was cooled with an ice bath and successively water (0.1 mL), THF (0.2 mL), a 15% aqueous NaOH (0.1 mL) and water (0.3 mL) were added. The precipitate obtained was filtered and washed with THF. The solvent of the filtrate was evaporated. The residue obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 71 mg of the title compound in solid form (yield: 47%).

Workup

  1. temperatureThe mixture was cooled with an ice bath
  2. temperatureIt was cooled with an ice bath
  3. customThe precipitate obtained
  4. filtrationwas filtered
  5. washwashed with THF
  6. customThe solvent of the filtrate was evaporated
  7. customThe residue obtained
  8. customwas purified by chromatography on silica gel
  9. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-deae21ca4c864e0e97f717509ca62e18
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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