Pyridine → 5-Bromo-4-chloro-2-isopropoxycarbonylamino-benzoic acid methyl ester

HRID 2353908Notes

Reaction equation

HRID 2353908 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([Cl:11])=[CH:6][C:5]=1[NH2:12].N1C=CC=CC=1.[CH:20]([O:23][C:24](Cl)=[O:25])([CH3:22])[CH3:21]>ClCCl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:24]([O:23][CH:20]([CH3:22])[CH3:21])=[O:25]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 53436879Methyl 2-amino-5-bromo-4-chlorobenzoate

Product 1

HCID 686794685-Bromo-4-chloro-2-isopropoxycarbonylamino-benzoic acid methyl esterYield 92%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-Amino-5-bromo-4-chloro-benzoic acid methyl ester (2.08 g, 7.86 mmol) and pyridine (1.91 ml, 23.6 mmol) in dichloromethane (75.0 ml) was added 1.00N isopropylchloroformate in toluene dropwise. The mixture was stirred for 16 hours at room temperature. The mixture washed with 0.500N HCl(aq) (100 ml), and brine (3×100 ml), then dried (Na2SO4) and concentrated to an oil. Purification by silica gel chromatography (gradient eluent, 0-10% ethyl acetate in hexane) provided 5-Bromo-4-chloro-2-isopropoxycarbonylamino-benzoic acid methyl ester (2.53 g, 92%) as a white crystalline material. MS (ES+): 350, 352 (M+H).

Workup

  1. washThe mixture washed with 0.500N HCl(aq) (100 ml), and brine (3×100 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to an oil
  4. customPurification by silica gel chromatography (gradient eluent, 0-10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0421f98e6dda4bdd8ebde184fd0830ac
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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