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Sodium Carbonate → 2-(2-(2-(3,5-Dimethylphenyl)-1H-indol-3-yl)ethyl)isoindoline-1,3-dione

HRID 1292374
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HRID 1292374 반응식
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][N:13]1[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]1=[O:23])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[C:29]([CH3:31])[CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:24][C:25]1[CH:26]=[C:27]([C:2]2[NH:3][C:4]3[C:9]([C:10]=2[CH2:11][CH2:12][N:13]2[C:21](=[O:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]2=[O:23])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:28]=[C:29]([CH3:31])[CH:30]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27343493,5-Dimethylphenylboronic acidHCID 109706542-[2-(2-bromo-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione

생성물 1

HCID 153130482-(2-(2-(3,5-Dimethylphenyl)-1H-indol-3-yl)ethyl)isoindoline-1,3-dione

시약·촉매·용매 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 702Ethanol용매
HCID 1140Toluene용매

실험 절차

To a solution of 2-[2-(2-bromo-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione (150 mg in a mixture of 5 mL toluene and 5 mL ethanol) was added 3,5-dimethylphenyl boronic acid (85 mg) followed by 1.0 mL of 1M sodium carbonate. To the stirred solution was added lithium chloride (60 mg) followed by tetrakis(triphenylphosphine) palladium (28 mg) and the mixture heated to reflux on an oil bath. After 4 hours the mixture was cooled to room temperature and concentrated in vacuo. Purification by flash chromatography on silica gel (hexane:ethyl acetate, 5:1) gave the title compound (146 mg).

후처리

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography on silica gel (hexane:ethyl acetate, 5:1)

출처 및 근거

ORD 기록
ord-7ebcaee8281f49a9ad5c93730cd4e890
출처 데이터셋
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05756507

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