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

HRID 382055

반응식

HRID 382055 반응식
Br[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:15]/[C:16]1[NH:17][CH:18]=[CH:19][C:20]=1[O:21][CH3:22])/[C:5](=[O:14])[NH:6]2.[NH:23]1[C:31]2[C:26](=[CH:27][C:28](B(O)O)=[CH:29][CH:30]=2)[CH:25]=[CH:24]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[NH:23]1[C:31]2[C:26](=[CH:27][C:28]([C:2]3[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]4[C:3]=3/[C:4](=[CH:15]/[C:16]3[NH:17][CH:18]=[CH:19][C:20]=3[O:21][CH3:22])/[C:5](=[O:14])[NH:6]4)=[CH:29][CH:30]=2)[CH:25]=[CH:24]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27343615-Indolylboronic 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 18363853(Z)-1,3-dihydro-4-(5-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A solution of (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one (112 mg, 0.31 mmol) (Starting Material 6), 5-indoleboronic acid (71 mg, 0.44 mmol) (from Example 40, Step A, supra) and sodium carbonate (110 mg, 1.03 mmol) were dissolved in 10 mL DMF and 5 mL water. The solution was degassed for 30 minutes by bubbling argon through the solution. At this time, dichlorobis(triphenylphosphine) palladium(II) (11 mg) (Aldrich) was added, and the reaction was heated, under argon, at 90° C. for 2 days. Water (20 mL) was then added and the precipitate was filtered off and dried. The product was purified via flash column chromatography (SiO2, 230-400 mesh) with 5% MeOH/CHCl3 to give (Z)-1,3-dihydro-4-(5-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one as a red powder. (Yield 38 mg, 76%).

후처리

  1. customThe solution was degassed for 30 minutes
  2. customby bubbling argon through the solution
  3. additionAt this time, dichlorobis(triphenylphosphine) palladium(II) (11 mg) (Aldrich) was added
  4. additionWater (20 mL) was then added
  5. filtrationthe precipitate was filtered off
  6. customdried
  7. customThe product was purified via flash column chromatography (SiO2, 230-400 mesh) with 5% MeOH/CHCl3

출처 및 근거

ORD 기록
ord-4981580049a0429ca5a3d03028f0acbd
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06307056B1

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