1H-Indol-6-ylboronic acid → (Z)-1,3-dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one

HRID 382065

반응식

HRID 382065 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][CH:28]=[C:29](B(O)O)[CH:30]=2)[CH:25]=[CH:24]1>CN(C=O)C.C(N(CC)CC)C>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([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:30]=2)[CH:25]=[CH:24]1

참가 물질

5

반응물 2

HCID 27632051H-Indol-6-ylboronic 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 18363899(Z)-1,3-dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one수율 57.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

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 (100 mg, 0.28 mmol) (Starting Material 6) and 6-indoleboronic acid (48 mg, 0.30 mmol) (from Example 48, Step A) were dissolved in 2 mL DMF and 2 mL triethylamine. The solution was degassed for 30 minutes by bubbling argon through the solution. At this time dichlorobis(triphenylphosphine) palladium(II) (20 mg, 0.029) (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 yield 64 mg (57%) (Z)-1,3-dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one as a red powder.

후처리

  1. customThe solution was degassed for 30 minutes
  2. customby bubbling argon through the solution
  3. additionAt this time dichlorobis(triphenylphosphine) palladium(II) (20 mg, 0.029) (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-709ceab2087e46eb99536e51b34c7ac0
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06307056B1

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