Aluminium lithium hydride → {2-[5-(2-Aminomethyl-4-fluorophenoxy)-indazol-1-yl]-ethyl}-dimethylamine

HRID 909237Notes

Reaction equation

HRID 909237 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:16]=3[C:17]#[N:18])=[CH:11][CH:12]=2)[CH:7]=[N:6]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:18][CH2:17][C:16]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:15]=1[O:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][CH2:3][N:2]([CH3:24])[CH3:1])[N:6]=[CH:7]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 674124802-[1-(2-dimethylaminoethyl)-1H-indazol-5-yloxy]-5-fluorobenzonitrile

Product 1

HCID 67411768{2-[5-(2-Aminomethyl-4-fluorophenoxy)-indazol-1-yl]-ethyl}-dimethylamineYield 113.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 2-[1-(2-dimethylaminoethyl)-1H-indazol-5-yloxy]-5-fluorobenzonitrile (0.115 g, 0.303 mmol) in THF (3 mL) was added LAH (0.61 mL of 1M in THF). The mixture was warmed to room temperature and stirred for 1.5 hours. The mixture was quenched with water (23 μL), 3N NaOH (23 μL) and water (69 μL). The salts were removed by filtration and the filtrate was concentrated under reduced pressure to afford 0.113 g of product (97% yield).

Workup

  1. customThe mixture was quenched with water (23 μL), 3N NaOH (23 μL) and water (69 μL)
  2. customThe salts were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1a3414d0272e4ace9d0b55834149d259
Source dataset
uspto-grants-2011_09
Patent number
US08017641B2

Reaction notes

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