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

HRID 382076Notes

Reaction equation

HRID 382076 reaction equation
[F:1][C:2]1[C:3](I)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:14][CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+].[OH:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[C:3]([C:29]2[CH:30]=[CH:31][C:26]([OH:25])=[CH:27][CH:28]=2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 18363869(Z)-1,3-dihydro-5-fluoro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×

Product 1

HCID 18363885(Z)-1,3-Dihydro-5-fluoro-4-(4-hydroxyphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of (Z)-1,3-dihydro-5-fluoro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (100 mg, 0.28 mmol) (Starting Material 12), 2M aqueous Na2CO3 solution (0.28 mL), (Ph3P)2PdCl2 (22.9 mg, 0.028 mmol) and 4-hydroxyphenylboronic acid (77.2 mg, 0.56 mmol) in 1,2-dimethoxyethane (10 mL) was heated at 104° C. for 2 days. The reaction mixture was filtered and concentrated. The crude material was purified by reverse phase HPLC to give (Z)-1,3-Dihydro-5-fluoro-4-(4-hydroxyphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 55mg, 61%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe crude material was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-a218fdbb42884e628f40fc0c267a6d33
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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