Aluminium lithium hydride → HCID 67357168, compound

HRID 268879Notes

Reaction equation

HRID 268879 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:16]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[CH2:17][CH2:18][OH:19])[CH:14]=2)[CH:9]=[N:8]1>C1COCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:17][CH2:18][OH:19])[CH:14]=2)[CH:9]=[N:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59831684HCID 59831684, compound

Product 1

HCID 67357168HCID 67357168, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −78° C. solution of 3-(1H-Indazol-6-yl)-3-pyridin-3-yl-acrylic acid ethyl ester CCXXXI (415 mg, 1.42 mmol) in THF (30 ml) was added 1 M solution of LiAlH4 (in THF, 2.81 ml) dropwise. The reaction mixture was stirred at room temperature for 1 hour and was quenched by addition of freshly ground Na2SO4.10H2O (2 g). After stirring for 30 minutes, the solid residue was filtered off and washed with EtOAc. The filtrate was dried over MgSO4, filtered, concentrated, and purified via flash chromatography (DCM/MeOH) affording 3-(1H-Indazol-6-yl)-3-pyridin-3-yl-prop-2-en-1-ol CCXXXII-A as a yellow oil (62 mg, 17% yield) in a first fraction, and 3-(1H-Indazol-6-yl)-3-pyridin-3-yl-propan-1-ol CCXXXII-B as a yellow foam (64 mg, 18% yield) in a second fraction.

Workup

  1. customwas quenched by addition of freshly ground Na2SO4.10H2O (2 g)
  2. stirringAfter stirring for 30 minutes
  3. filtrationthe solid residue was filtered off
  4. washwashed with EtOAc
  5. dry with materialThe filtrate was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified via flash chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-a84e3bb945314cd4b3bc88b3c8b6d047
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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