Ammonium Chloride → 3-iodo-1-((2-methylthiazol-5-yl)methyl)-1H-indazol-4-amine
Reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-])=O)[N:4]([CH2:14][C:15]2[S:19][C:18]([CH3:20])=[N:17][CH:16]=2)[N:3]=1.[Cl-].[NH4+]>CCO.O.[Fe]>[I:1][C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH2:14][C:15]2[S:19][C:18]([CH3:20])=[N:17][CH:16]=2)[N:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
To a solution of 5-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-2-methylthiazole (332 mg, 0.830 mmol) in EtOH/water (4:1, 10 mL) was added iron powder (463 mg, 8.30 mmol) and ammonium chloride (44.4 mg, 0.83 mmol). The resulting mixture was heated at 85° C. with vigorous magnetic stirring for three hours. The mixture was cooled to ambient temperature, concentrated, and EtOAc (40 mL) and triethylamine (10 mL) were added. The resulting mixture was heated at 85° C. for 20 minutes, then cooled to 45° C., filtered through a Celite plug, and the plug was rinsed with MeOH (30 mL). The combined organic filtrates were concentrated, the residue was extracted with DCM (3×30 mL), the combined organic extracts dried over sodium sulfate, filtered and concentrated to afford the desired product (307 mg).
Workup
- temperatureThe mixture was cooled to ambient temperature
- concentrationconcentrated
- additionEtOAc (40 mL) and triethylamine (10 mL) were added
- temperatureThe resulting mixture was heated at 85° C. for 20 minutes
- temperaturecooled to 45° C.
- filtrationfiltered through a Celite plug
- washthe plug was rinsed with MeOH (30 mL)
- concentrationThe combined organic filtrates were concentrated
- extractionthe residue was extracted with DCM (3×30 mL)
- dry with materialthe combined organic extracts dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c64442782f0648b3a4230b0363e5599c
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174981B2
Reaction notes
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