Boronic acid, [3-[(2-amino-2-oxoethyl)amino]phenyl]- → HCID 54413821, compound

HRID 382078Notes

Reaction equation

HRID 382078 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][C:17]=1[O:18][CH3:19].[C:21]([CH2:24][NH:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)(=[O:23])[NH2:22]>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:30]2[CH:31]=[C:26]([NH:25][CH2:24][C:21]([NH2:22])=[O:23])[CH:27]=[CH:28][CH:29]=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][C:17]=1[O:18][CH3:19]

Participants

5

Reactant 2

HCID 18363893Boronic acid, [3-[(2-amino-2-oxoethyl)amino]phenyl]-HCID 18363902(3Z)-5-fluoro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylidene]-2,3-dihydro-1H-indol-2-one3×

Product 1

HCID 54413821HCID 54413821, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of (Z)-1,3-dihydro-5-fluoro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (50 mg, 0.13 mmol), 2M aqueous Na2CO3 solution (0.13 mL) (Starting Material 13), (Ph3P)2PdCl2 (22 mg, 0.027 mmol) and 3-(carbamoylmethyl-amino)-phenylboronic acid (55 mg, 0.26 mmol) in 1,2-dimethoxyethane (5 mL) was heated at 103° C. for 3 days. The reaction mixture was filtered and concentrated. The crude material was purified by C18 reverse phase chromatography to give 2-[3-[5-Fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-2,3-dihydro-1H-indol-4-yl]-phenylamino]-acetamide. (Yield 1 5mg, 28%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe crude material was purified by C18 reverse phase chromatography

Sources & evidence

ORD record
ord-ffa42b3c143e49c596266a9695725ec2
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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