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

HRID 1458334
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HRID 1458334 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.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>[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
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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 178418397
HCID 178418397, 화합물
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-6f01e3c9e75649c1887b3fcda9a35afc
출처 데이터셋
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05849764

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