Aluminium lithium hydride → HCID 178511315, compound

HRID 1638084Notes

Reaction equation

HRID 1638084 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

Conditions

Temperature
0 °C

Procedure

To a solution of [4-(6-fluoro-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, 1.0 M 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. customthe reaction was carefully quenched with water (4.0 ml)
  5. customThe solids were removed via filtration
  6. washwashed with THF
  7. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-691ea2b4319b470298064ff658173900
Source dataset
uspto-grants-2000_03
Patent number
US06043240

Reaction notes

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