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

HRID 1897519Notes

Reaction equation

HRID 1897519 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-0475c5b1f5fd425ab8bed9e9e9f2425f
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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