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

Reaction equation

HRID 382065 reaction equation
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

Participants

5

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-709ceab2087e46eb99536e51b34c7ac0
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Linked notes

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