Aluminium lithium hydride → HCID 69182746, compound

HRID 2373216Notes

Reaction equation

HRID 2373216 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[C:10]([C:14]2[C:19]([C:20](OCC)=[O:21])=[C:18]([CH3:25])[N:17]=[C:16]3[N:26]([CH2:29][CH3:30])[N:27]=[CH:28][C:15]=23)[CH:11]=[N:12][CH:13]=1>C(OCC)C>[Br:7][C:8]1[CH:9]=[C:10]([C:14]2[C:19]([CH2:20][OH:21])=[C:18]([CH3:25])[N:17]=[C:16]3[N:26]([CH2:29][CH3:30])[N:27]=[CH:28][C:15]=23)[CH:11]=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69182098HCID 69182098, compound

Product 1

HCID 69182746HCID 69182746, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a stirred suspension of lithium aluminum hydride (8.8 mg) in diethyl ether (0.5 ml) was added a solution of ethyl 4-(5-bromo-3-pyridyl)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (30 mg) in diethyl ether (1.5 ml) at −78° C. The mixture was gradually warmed to −10° C. over 8 hours and quenched with water at −10° C. The mixture was filtered through celite pad, and the filtrate was evaporated. The residue was purified by preparative thin layer chromatography eluting with a mixture of EtOAc and n-hexane (2:1) to give [4-(5-bromo-3-pyridyl)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl]methanol (18 mg) as a colorless crystal.

Workup

  1. customquenched with water at −10° C
  2. filtrationThe mixture was filtered through celite pad
  3. customthe filtrate was evaporated
  4. customThe residue was purified by preparative thin layer chromatography
  5. washeluting with a mixture of EtOAc and n-hexane (2:1)

Sources & evidence

ORD record
ord-a388893d8e1146fa902215cdfc4cc210
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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