Pyridine → [3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl ester

HRID 1784841Notes

Reaction equation

HRID 1784841 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=[C:6]([Br:8])[CH:7]=1.N1C=CC=CC=1.[CH3:23][O:24][C:25](Cl)=[O:26]>ClC(Cl)C.ClCCl>[CH3:23][O:24][C:25](=[O:26])[NH:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 50994432(3-Amino-5-bromo-phenyl)-pyridin-3-yl-methanone

Product 1

HCID 50994354[3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl esterYield 86%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 0.20 g of (3-amino-5-bromo-phenyl)-pyridin-3-yl-methanone (0.72 mmol) in 5 mL of dichloroethane was added 0.58 mL of pyridine and 0.55 mL of methylchloroformate, and the mixture was heated to 60° C. for 20 minutes. The reaction was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate, dried over NaSO4 and the volatiles were removed under reduced pressure to give 208 mg (86% yield) of [3-bromo-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl ester.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over NaSO4
  3. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-e49b47b5d77249859658952d70194642
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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