4-{3E-[5-(2-amino-phenylethynyl)-2,4-dimethoxy-phenyl]acryloyl}-N-(3-imidazol-1-ylpropyl)benzenesulfonamide → N-(3-Imidazol-1-yl-propyl)-4-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxy-phenyl]acryloyl}benzenesulfonamide

HRID 347371Notes

Reaction equation

HRID 347371 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]#[C:9][C:10]1[C:11]([O:40][CH3:41])=[CH:12][C:13]([O:38][CH3:39])=[C:14](/[CH:16]=[CH:17]/[C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH:29][CH2:30][CH2:31][CH2:32][N:33]3[CH:37]=[CH:36][N:35]=[CH:34]3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])[CH:15]=1>C(#N)C.[Pd](Cl)Cl>[N:33]1([CH2:32][CH2:31][CH2:30][NH:29][S:26]([C:23]2[CH:22]=[CH:21][C:20]([C:18](=[O:19])/[CH:17]=[CH:16]/[C:14]3[CH:15]=[C:10]([C:9]4[NH:1][C:2]5[C:3]([CH:8]=4)=[CH:4][CH:5]=[CH:6][CH:7]=5)[C:11]([O:40][CH3:41])=[CH:12][C:13]=3[O:38][CH3:39])=[CH:25][CH:24]=2)(=[O:28])=[O:27])[CH:37]=[CH:36][N:35]=[CH:34]1

Participants

4

Reactant 1

HCID 694879324-{3E-[5-(2-amino-phenylethynyl)-2,4-dimethoxy-phenyl]acryloyl}-N-(3-imidazol-1-ylpropyl)benzenesulfonamide

Product 1

HCID 11467239N-(3-Imidazol-1-yl-propyl)-4-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxy-phenyl]acryloyl}benzenesulfonamideYield 100%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-{3E-[5-(2-amino-phenylethynyl)-2,4-dimethoxyphenyl]acryloyl}-N-(3-imidazol-1-ylpropyl)benzenesulfonamide (Ex-50A, 210 mg, 0.37 mmol) in acetonitrile (130 mL) was purged with nitrogen gas for 10 minutes. Palladium(II) chloride (5.0 mg, 0.029 mmol) was added to the reaction vessel. The reaction mixture was refluxed for 16 hrs. The cooled reaction mixture was stirred with 3-mercaptopropyl functionalized silica gel (500 mg) for 5 minutes. The filtrate was collected via suction filtration and concentrated to an orange solid to give 210 mg (100%) of the title compound, mp 197–200° C. 1H-NMR (300 MHz, DMSO-d6) 11.19 (br s, 1H), 8.28 (m, 3H), 8.11 (m, 2H), 7.95 (m, 4H), 7.45 (m, 3H), 7.00 (m, 5H), 4.08 (s, 3H), 4.03 (s, 3H), 3.89 (m, 2H), 2.69 (br s, 2H), 1.78 (br s, 2H). HRMS (ESI) Calcd. for C31H30N4O5S: 571.2015 [(M+H)+]; Found: 571.2016.

Workup

  1. customwas purged with nitrogen gas for 10 minutes
  2. temperatureThe reaction mixture was refluxed for 16 hrs
  3. customThe cooled reaction mixture
  4. filtrationThe filtrate was collected via suction filtration
  5. concentrationconcentrated to an orange solid

Sources & evidence

ORD record
ord-a0572ba6cf0b4e219fd8e8fcc6bfd63e
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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