Ethyl chloroformate → HCID 68827005, compound

HRID 230750Notes

Reaction equation

HRID 230750 reaction equation
N[C:2]1[C:7]([Br:8])=[CH:6][N:5]=[C:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:3]=1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(Cl)Cl.N1C=CC=CC=1>[Br:8][C:7]1[C:2]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:3][C:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 68825126HCID 68825126, compound

Product 1

HCID 68827005HCID 68827005, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-amino-5-bromopicolinate (546 mg, 2 mmol) in CH2Cl2 (5 mL) and pyridine (1 mL) at 0° C., was added ethyl chloroformate (271 mg, 2.5 mmol). The mixture was stirred at rt for 2 h, diluted with dichloromethane, washed with 5% citric acid, and sat. K2HPO4 aq. solution. The organic layer was dried over MgSO4 and the product was purified by flash column chromatography (SiO2, eluting with 20% EtOAc/CH2Cl2) to give a white solid (570 mg, 83%). LC-MS: m/z 345 (M+).

Workup

  1. washwashed with 5% citric acid, and sat. K2HPO4 aq. solution
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe product was purified by flash column chromatography (SiO2, eluting with 20% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-69d3d33fa1bb47348aa3e7432d08575e
Source dataset
uspto-grants-2009_07
Patent number
US07566784B2

Reaction notes

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