2-Chloro-5-nitropyridine → HCID 67235239, compound
Reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH3:3].CC([O-])(C)C.[K+].Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=1>CS(C)=O>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:11][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=2)[CH:8]=[CH:9][CH:10]=1)[CH3:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a solution of 3-[(1-methylethyl)oxy]phenol (Intermediate 27, 456 mg) in DMSO (8 mL) was added t-BuOK (336 mg, 3 mmol, Acros). The reaction mixture was stirred at 20° C. for 30 minutes. 2-chloro-5-nitropyridine (474 mg, 3 mmol, Aldrich) was added and the resulting mixture was stirred at 120° C. for 2 hours. The reaction mixture was cooled to room temperature, poured into ice-water (50 mL) and extracted with dichloromethane (3 times 50 mL). The combined organic layers were dried over sodium sulphate, filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with (PE:EtOAc=50:1) to afford the title compound as a light yellow solid (670 mg).
Workup
- stirringthe resulting mixture was stirred at 120° C. for 2 hours
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with dichloromethane (3 times 50 mL)
- dry with materialThe combined organic layers were dried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel eluting with (PE:EtOAc=50:1)
Sources & evidence
- ORD record
- ord-225e719e9b8e4c3583e5f9af228f5a92
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722695B2
Reaction notes
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