Triethylamine → tert-Butyl 2-chloropyridin-4-yl(3-nitrophenyl)carbamate
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.CCN(CC)CC.[O:25](C(OC(C)(C)C)=O)[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=O>C1COCC1.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:26](=[O:25])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:5]=[CH:4][N:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a stirring solution of 2-Chloro-N-(3-nitrophenyl)pyridine-4-amine (2.70 g, 10.82 mmol) in THF (45 mL) was added Et3N (6.32 mL, 45.3 mmol). The mixture was cooled to 0° C., and DMAP (0.0135 g, 0.110 mmol) and BOC2O (2.84 g, 12.99 mmol) were added. The mixture was warmed to rt and stirred for 18 h. The mixture was quenched with ice and diluted with water. Extracted with EtOAc (3×200 mL), washed with brine and water, dried (MgSO4), and concentrated. A dark oil was afforded, which was passed through a pad of silica gel, eluting with 1:1 EtOAc/hexanes. Concentrated and dried under high vacuum to afford tert-Butyl 2-chloropyridin-4-yl(3-nitrophenyl)carbamate (3.65 g, 96.5% yield).
Workup
- temperatureThe mixture was warmed to rt
- customThe mixture was quenched with ice
- additiondiluted with water
- extractionExtracted with EtOAc (3×200 mL)
- washwashed with brine and water
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customA dark oil was afforded
- washeluting with 1:1 EtOAc/hexanes
- concentrationConcentrated
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-a0992cf4abfd4e18b04f29549e8aa965
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328103B2
Reaction notes
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