2-Hex-3-en-3-yl-1,3,2-benzodioxaborole → 2-[2-(-1-Ethyl-but-1-enyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid ethyl ester

HRID 1047769노트

반응식

HRID 1047769 반응식
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2I)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[CH2:26]([C:28](B1OC2C=CC=CC=2O1)=[CH:29][CH2:30][CH3:31])[CH3:27]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[C:28]([CH2:26][CH3:27])=[CH:29][CH2:30][CH3:31])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 50468522-Hex-3-en-3-yl-1,3,2-benzodioxaboroleHCID 593141532-(2-Iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

생성물 1

HCID 685911652-[2-(-1-Ethyl-but-1-enyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid ethyl ester수율 146.8%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (400 mg, 0.89 mmol) and 2-(1-Ethyl-but-1-enyl)-benzo[1,3,2]dioxaborole (709 μL, 3.56 mmol) in dioxane (15 mL) is added Pd(PPh3)4 (103 mg, 8.9% mmol) and 2M aqueous solution of CsCO3 (1.34 mL, 2.67 mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 110° C., 2 h. After concentration in vacuo, the residue is purified by flash column chromatography (120 g silica gel, gradient elution: 5%-50% EtOAc in heptane) to give a pure product (128) as a brown semi-solid (530 mg, 73%).

후처리

  1. customThe resulting reaction mixture
  2. customrun in a microwave reaction
  3. custom110° C., 2 h
  4. concentrationAfter concentration in vacuo
  5. customthe residue is purified by flash column chromatography (120 g silica gel, gradient elution: 5%-50% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-b3dfef23d1ea4d1f962aa1af8830ce7d
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569535B2

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