Potassium Hydroxide → 1,4-dimethyl-5-(2-phenoxy-phenyl)-1H-pyrrole-3-carboxylic acid (4-methanesulfonyl-phenyl)-amide

HRID 912585

Reaktionsgleichung

Reaktionsgleichung von HRID 912585
[S:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[C:15]([CH3:21])=[C:16](Br)[N:17]([CH3:19])[CH:18]=2)=[O:13])=[CH:7][CH:6]=1)(=[O:4])(=[O:3])N.[O:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[K+].[CH2:40](O)C.CN(C=O)C>CC(O)=O.CC(O)=O.C1CCC([N-]C2CCCCC2)CC1.C1CCC([N-]C2CCCCC2)CC1.[Pd+2]>[CH3:40][S:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[C:15]([CH3:21])=[C:16]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:17]([CH3:19])[CH:18]=2)=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Komponenten

6

Edukt 4

HCID 14797Potassium HydroxideHCID 2773559(2-Phenoxyphenyl)boronic acidHCID 19794673N,N-dimethylformamide ethanolHCID 672538152-Bromo-1,3-dimethyl-1H-pyrrole-4-carboxylic acid [4-(sulfamoyl)phenyl]-amide

Produkt 1

HCID 598076411,4-dimethyl-5-(2-phenoxy-phenyl)-1H-pyrrole-3-carboxylic acid (4-methanesulfonyl-phenyl)-amideAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11180781trans-Bis(dicyclohexylamine)palladium(II) acetateKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Into a 50 mL round bottom flask was weighed 100 mg of 2-Bromo-1,3-dimethyl-1H-pyrrole-4-carboxylic acid [4-(sulfamoyl)phenyl]-amide (0.27 mmol), 230 mg of (2-phenoxy)phenylboronic acid, potassium hydroxide (30.2 mg, 0.54 mmol), and DAPCy (J. Org Chem (2004), 69: 4330-4335) (6.2 mg, 4 Mol %) and Ethanol/DMF (3 ml, 50:50) was added. The solution was heated at 100° C. overnight. The reaction was cooled and washed into a separatory funnel with ethyl acetate and water. The ethyl acetate washed with water and brine, then was dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2), eluting with EtOAc/Hex 0-80% to afford the title compounds as a white solid (10 mg, 8%); 1H NMR (DMSO-d6): δ 7.88 (d, J=9 Hz, 2H), 7.77 (d, J=9 Hz, 2H), 7.60 (s, 1H), 7.43-7.37 (m, 1H), 7.32-7.20 (m, 4H), 7.04 (d, J=9 Hz, 2H), 6.85 (d, J=8 Hz, 2H), 3.52 (s, 3H), 3.04 (s, 3H), 2.20 (s, 3H); MS (ESI) m/z 461 [M+H]+

Aufarbeitung

  1. customInto a 50 mL round bottom flask was weighed
  2. temperatureThe reaction was cooled
  3. washwashed into a separatory funnel with ethyl acetate and water
  4. washThe ethyl acetate washed with water and brine
  5. dry with materialwas dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by flash chromatography (SiO2)
  8. washeluting with EtOAc/Hex 0-80%

Quellen und Nachweise

ORD-Eintrag
ord-e18caa7accb84a58a529e970ea4ce174
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026237B2

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