Aluminium lithium hydride → HCID 178511315, compound

HRID 1420429Notes

Reaction equation

HRID 1420429 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]#[N:19])[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][NH2:19])[CH2:15][CH2:16]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178511314HCID 178511314, compound

Product 1

HCID 178511315HCID 178511315, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(6fluoro-1H-indazol-3-yl)-1-piperidinyl]-acetonitrile (6.1 g, 23.6 mmol) in dry THF (235 ml) was added (dropwise) lithium aluminum hydride (LAH) (28.4 mmol, 1.0M in THF) at room temperature, under nitrogen. Upon complete addition, the reaction mixture was warmed to reflux for 3 hours. After cooling to 0 C. in an ice bath, the reaction was carefully quenched with water (4.0 ml). The solids were removed via filtration and washed with THF. The combined filtrates were concentrated to give 5.6 g of the desired product. This material was suspended in DCM and filtered to give the product as an off-white solid, m.p. 125°-128° C.

Workup

  1. additionUpon complete addition
  2. temperaturethe reaction mixture was warmed
  3. temperatureto reflux for 3 hours
  4. temperatureAfter cooling to 0 C
  5. customin an ice bath, the reaction was carefully quenched with water (4.0 ml)
  6. customThe solids were removed via filtration
  7. washwashed with THF
  8. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-690454de2d2446b289414bc4f18ce8d2
Source dataset
uspto-grants-1999_03
Patent number
US05889035

Reaction notes

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