Water → 3-(4-amino-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-5-yl)-4-methoxybenzonitrile
Reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[C:11]1[N:15]([CH2:16][CH2:17][O:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:14]=[CH:13][C:12]=1[N+:24]([O-])=O.O.[Cl-].[NH4+]>C(O)C.ClCCl.[Fe]>[NH2:24][C:12]1[CH:13]=[N:14][N:15]([CH2:16][CH2:17][O:18][CH2:19][Si:20]([CH3:21])([CH3:23])[CH3:22])[C:11]=1[C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[O:2][CH3:1])[C:7]#[N:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 75 °C
Procedure
To a solution of 4-methoxy-3-(4-nitro-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-5-yl)benzonitrile (900 mg, 2.4 mmol) in 25 mL ethanol was added 50 mL water, ammonium chloride (636 mg, 12 mmol), and iron powder (806 mg, 14 mmol). The reaction mixture was stirred at 75° C. for 6 hours. After cooling to room temperature, the reaction was diluted with dichloromethane and filtered through a celite pad, rinsing with more dichloromethane. The filtrate was added to 150 mL saturated aqueous sodium bicarbonate and extracted twice with dichloromethane. The combined organic extracts were dried over magnesium sulfate and concentrated to yield 717 mg (84%) of 3-(4-amino-1-(2-((trimethylsilyl)methoxy)ethyl)-1H-pyrazol-5-yl)-4-methoxybenzonitrile, which was carried forward without purification. LCMS (ESI) m+H=375.1.
Workup
- temperatureAfter cooling to room temperature
- filtrationfiltered through a celite pad
- washrinsing with more dichloromethane
- additionThe filtrate was added to 150 mL saturated aqueous sodium bicarbonate
- extractionextracted twice with dichloromethane
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-44ac5455c3af4c5b863108ffdec2c941
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999998B2
Reaction notes
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