3-Bromo-4-methoxybenzoic acid → 2-(3-Bromo-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl ester

HRID 2094711노트

반응식

HRID 2094711 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.Cl.[CH3:14][O:15][C:16]([C:18]1([NH2:27])[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)=[O:17]>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:14][O:15][C:16]([C:18]1([NH:27][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:2]([Br:1])[CH:3]=2)[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)=[O:17]

참가 물질

5

반응물 2

HCID 668363-Bromo-4-methoxybenzoic acidHCID 45074056methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochloride

생성물 1

HCID 670763302-(3-Bromo-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl ester수율 81.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 24386Thionyl Chloride용매

반응 조건

온도
60 °C

실험 절차

3-Bromo-4-methoxybenzoic acid (22.8 g, 98.8 mmol) was dissolved in thionyl chloride (42 ml) and stirred at 60° C. for 30 min. The volatiles were evaporated in vacuo and the residue was stripped with dioxane. The obtained acid chloride was dissolved in DCM (50 ml). 2-Amino-indane-2-carboxylic acid methyl ester hydrochloride (15.0 g, 65.9 mmol) was suspended in DCM (100 ml), EDIA (10.2 g, 79.1 mmol) was added, the mixture was cooled in an ice bath, and the solution of the acid chloride was slowly added. The mixture was stirred overnight at room temperature and evaporated to dryness. The residue was purified by silica gel chromatography (DCM/methanol gradient) and subsequent crystallization from EA to give 21.8 g of the title compound.

후처리

  1. customThe volatiles were evaporated in vacuo
  2. dissolutionThe obtained acid chloride was dissolved in DCM (50 ml)
  3. additionEDIA (10.2 g, 79.1 mmol) was added
  4. temperaturethe mixture was cooled in an ice bath
  5. stirringThe mixture was stirred overnight at room temperature
  6. customevaporated to dryness
  7. customThe residue was purified by silica gel chromatography (DCM/methanol gradient) and subsequent crystallization from EA

출처 및 근거

ORD 기록
ord-b2e746e2f2054cbd8d1762945a560a71
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445530B2

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