Ammonium Chloride → 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amine

HRID 706623Notes

Reaction equation

[CH:1]([C:4]1[N:9]=[C:8]([CH2:10][N:11]2[C:19]3[C:14](=[C:15]([N+:20]([O-])=O)[CH:16]=[CH:17][CH:18]=3)[C:13]([CH3:23])=[N:12]2)[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Cl-].[NH4+]>CCO.O.[Fe]>[CH:1]([C:4]1[N:9]=[C:8]([CH2:10][N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([NH2:20])[C:14]=3[C:13]([CH3:23])=[N:12]2)[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole (1.51 g, 4.87 mmol) in EtOH/H2O (40 mL/10 mL) was added iron (5.43 g, 97.3 mmol) and ammonium chloride (0.260 g, 4.87 mmol). The reaction mixture was heated to reflux for three hours, then cooled to 60° C. and filtered through a pad of Celite®. The filter cake was washed with EtOH/Et3N (20:1, 200 mL) and MeOH/DCM (1:1, 100 mL). The filtrate was concentrated, and the residue was dissolved in EtOAc (200 mL). The ethyl acetate was washed with NaHCO3, dried (Na2SO4), filtered and concentrated to give the desired product (57%).

Workup

temperatureThe reaction mixture was heated
temperatureto reflux for three hours
filtrationfiltered through a pad of Celite®
washThe filter cake was washed with EtOH/Et3N (20:1, 200 mL) and MeOH/DCM (1:1, 100 mL)
concentrationThe filtrate was concentrated
dissolutionthe residue was dissolved in EtOAc (200 mL)
washThe ethyl acetate was washed with NaHCO3
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-76817e01fd444095aebeb226376410a5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174981B2

Reaction notes

Loading…