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

HRID 1835332Notes

Reaction equation

HRID 1835332 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

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 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.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customwas followed by evaporation of the solvent in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c7eaa289b2f04a148facabf51e28c28f
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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