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

HRID 521484

反応式

HRID 521484 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24386Thionyl Chloride溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-30e0985f63e94214b75c8d1c2a4714ff
出典データセット
uspto-grants-2016_05
特許番号
US09328071B2

関連ノート

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