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

HRID 382048Notes

Reaction equation

HRID 382048 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]2[C:13]=1/[C:14](=[CH:25]/[C:26]1[NH:27][CH:28]=[CH:29][C:30]=1[O:31][CH3:32])/[C:15](=[O:24])[NH:16]2.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]3[C:13]=2/[C:14](=[CH:25]/[C:26]2[NH:27][CH:28]=[CH:29][C:30]=2[O:31][CH3:32])/[C:15](=[O:24])[NH:16]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic 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 9951621(Z)-1,3-dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-oneYield 52%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Using Method S above, 4-hydroxyphenyl boronic acid (85.0 mg, 0.62 mmol) (see Gilman, supra) 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 1 day to give (Z)-1,3-dihydro-4-(4-hydroxyphenyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one (yield: 11 0 mg, 52%).

Workup

  1. temperatureat reflux for 1 day

Sources & evidence

ORD record
ord-f2690117b6634c73a5f3c1b4edf3150d
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

Loading…