Dimethylformamide → HCID 178433228, compound

HRID 382075Notes

Reaction equation

HRID 382075 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:17][CH:16]=[N:15][C:14]=1[CH3:18].[C:20]([O-:23])([O-])=O.[Na+].[Na+].[C:26]([C:30]1C(C)=C(B(O)OO[SiH3])C=[CH:34][C:35]=1C)(C)(C)[CH3:27].CN(C=O)C>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.COCCOC>[F:1][C:2]1[C:3]([C:26]2[CH:30]=[CH:35][CH:34]=[C:20]([OH:23])[CH:27]=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:17][CH:16]=[N:15][C:14]=1[CH3:18]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 178423579HCID 178423579, compoundHCID 178433242HCID 178433242, compound2×

Product 1

HCID 178433228HCID 178433228, 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-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (50 mg, 0.135 mmol) (Starting Material 11), 2M aqueous Na2CO3 solution (0.14 mL), (Ph3P)2PdCl2 (11 mg, 0.0135 mmol) and 3-tert-butyl-dimethyl-silyloxy-phenylboronic acid (0.14 g, 0.54 mmol) in 5 ml of a 1:4 mixture of DMF:1,2-dimethoxyethane (5 mL) was heated at 104° C. for 3 days. The reaction mixture was concentrated and the crude material was washed with methanol to give (Z)-1,3-Dihydro-5-fluoro-4-(3-hydroxyphenyl)-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one. (Yield 10 mg, 22%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe crude material was washed with methanol

Sources & evidence

ORD record
ord-53da89012eaa4e90b388c0727cd0988d
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

Loading…