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

反応式

HRID 382065 の反応式
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

参加物

5

反応物 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-one2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-709ceab2087e46eb99536e51b34c7ac0
出典データセット
uspto-grants-2001_10
特許番号
US06307056B1

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