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

HRID 2112224Notes

Reaction equation

HRID 2112224 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-36ac06d819f94268858b79a14d6a06a0
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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