Sodium Carbonate → (Z)-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-4-phenyl-2H-indol-2-one

HRID 382049

반응식

HRID 382049 반응식
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16]2[C:12]=1/[C:13](=[CH:24]/[C:25]1[NH:26][CH:27]=[CH:28][C:29]=1[O:30][CH3:31])/[C:14](=[O:23])[NH:15]2.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH3:31][O:30][C:29]1[CH:28]=[CH:27][NH:26][C:25]=1/[CH:24]=[C:13]1\[C:14](=[O:23])[NH:15][C:16]2[C:12]\1=[C:11]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=2

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 18359293(Z)-1,3-dihydro-4-bromo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one2회

생성물 1

HCID 9820311(Z)-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-4-phenyl-2H-indol-2-one수율 81%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

Using Method S above, phenyl boronic acid (75.2 mg, 0.617 mmol) (Aldrich) was coupled with (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one (150 mg, 0.41 mmol) (Starting Material 6) using DPPFPdCl2 (17 mg) (Aldrich) as catalyst in aqueous 2M Na2CO3 (0.42 mL, 0.84 mmol) and DME (15 mL) at reflux for 18 h to give (Z)-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-4-phenyl-2H-indol-2-one (yield: 120 mg, 80%).

후처리

  1. temperatureat reflux for 18 h

출처 및 근거

ORD 기록
ord-e9af2b3cc1614913b43afca8f983d3c2
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06307056B1

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