(4-{3E-[5-(2-amino-phenylethynyl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonylamino)acetic acid → (4-{3E-[5-(1H-Indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonylamino)acetic acid

HRID 347373Notes

Reaction equation

HRID 347373 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:36][CH3:37])=[CH:12][C:13]([O:34][CH3:35])=[C:14](/[CH:16]=[CH:17]/[C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH:29][CH2:30][C:31]([OH:33])=[O:32])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])[CH:15]=1>C(#N)C.C(O)C.[Pd](Cl)Cl>[NH:1]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:8]=[C:9]1[C:10]1[C:11]([O:36][CH3:37])=[CH:12][C:13]([O:34][CH3:35])=[C:14](/[CH:16]=[CH:17]/[C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH:29][CH2:30][C:31]([OH:33])=[O:32])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])[CH:15]=1

Participants

5

Reactant 1

HCID 69488015(4-{3E-[5-(2-amino-phenylethynyl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonylamino)acetic acid

Product 1

HCID 11168363(4-{3E-[5-(1H-Indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonylamino)acetic acidYield 23%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of (4-{3E-[5-(2-amino-phenylethynyl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonylamino)acetic acid (Ex-51A, 153 mg, 0.294 mmol) in acetonitrile (130 mL) was purged with nitrogen gas for 10 minutes. Palladium (II) chloride (5.2 mg, 0.029 mmol) was added to the reaction vessel. The reaction mixture was refluxed for 2 h. The reaction mixture was gravity filtered and yielded a red solid. The crude was swished in ethanol to give 35 mg (23%) of the title compound as a red solid, mp 189–190° C. 1H-NMR (300 MHz, DMSO-d6) 11.18 (br s, 1H), 8.25 (m, 3H), 8.06 (d, 1H, J=15.3 Hz), 7.89 (m, 5H), 7.49 (d, 1H, J=7.8 Hz), 7.41 (d, 1H, J=8.1 Hz), 7.03 (t, 1H, J=6.6 (m, 1H), 6.83 (s, 1H), 4.04 (s, 3H), 3.99 (s, 3H). MS (ESI, for C27H24N2O7S) Found: 520 [(M+H)+].

Workup

  1. customwas purged with nitrogen gas for 10 minutes
  2. temperatureThe reaction mixture was refluxed for 2 h
  3. filtrationfiltered
  4. customyielded a red solid

Sources & evidence

ORD record
ord-11522c447138406a83814e6559e5b893
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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