tert-Butanol → [6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-carbamic acid tert-butyl ester

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:5](C(O)=O)=[CH:4][N:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.C([N:37]([CH2:40]C)CC)C.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:42]([O:46][C:40](=[O:25])[NH:37][C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:10][C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])([CH3:45])([CH3:44])[CH3:43]

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 235028066-Chloro-4-(2-chloro-phenyl)-nicotinic acid

Product 1

HCID 87890758[6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-carbamic acid tert-butyl esterYield 85%

Procedure

A mixture of 650 mg (2.42 mmol) 6-chloro-4-(2-chloro-phenyl)-nicotinic acid, 0.54 ml (2.42 mmol) diphenylphosphoryl azide, 0.34 ml (2.42 mmol) triethylamine and 8 ml tert-butanol was heated at reflux for 1 h. Cooling to room temperature was followed by evaporation of the solvent in vacuo. The residue was dissolved in ethyl acetate and washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried with sodium sulfate and concentrated. Column chromatography gave 695 mg (85%) of the title compound as a white solid.