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

HRID 2353908
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반응식

HRID 2353908 반응식
[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]
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344
Dichloromethane
용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0421f98e6dda4bdd8ebde184fd0830ac
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07749992B2

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