Potassium Carbonate → 3-(pyridin-3-yl)-N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)acrylamide

HRID 1754114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1754114
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:5]=[C:6]([S:10]([C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=[CH:29][C:30](Cl)=[O:31])[CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=[CH:29][C:30]([NH:17][C:16]2[CH:18]=[CH:19][C:13]([S:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:1])([F:20])[F:21])[CH:5]=3)(=[O:12])=[O:11])=[CH:14][CH:15]=2)=[O:31])[CH:23]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 533991563-Pyridineacrylic acid chlorideHCID 891567704-((3-(Trifluoromethoxy)phenyl)sulfonyl)aniline

Produkt 1

HCID 779617403-(pyridin-3-yl)-N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)acrylamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 4-((3-(trifluoromethoxy)phenyl)sulfonyl)aniline (86, 0.27 mmol) in DMF (3 mL) is added 3-(pyridin-3-yl)acryloyl chloride (58 mg, 0.28 mmol) and K2CO3 (138 mg, 1 mmol). The mixture is heated at 50° C. for 2 h and the solvent is evaporated. The residue is partitioned between EtOAc (15 mL) and brine (10 mL) and the layers are separated. The aqueous layer is extracted with EtOAc (10 mL) and the combined extracts are dried (Na2SO4) and evaporated. Purification of the residue by preparative TLC with 100:5:0.5 CH2Cl2/MeOH/NH4OH gives the titled compounds as a white solid (60 mg, 50%). (LC_MS: M+1 449.14; 1HNMR (400 MHz, DMSO-d6): δ 10.76 (s, 1H), 8.82 (d, 1H), 8.57 (dd, 1H), 7.89-8.06 (m, 7H), 7.76 (t, 1H), 7.74 (m, 1H), 7.66 (d, 1H), 7.46 (dd, 1H), 6.91 (d, 1H).

Aufarbeitung

  1. customthe solvent is evaporated
  2. customThe residue is partitioned between EtOAc (15 mL) and brine (10 mL)
  3. customthe layers are separated
  4. extractionThe aqueous layer is extracted with EtOAc (10 mL)
  5. dry with materialthe combined extracts are dried (Na2SO4)
  6. customevaporated
  7. customPurification of the residue by preparative TLC with 100:5:0.5 CH2Cl2/MeOH/NH4OH

Quellen und Nachweise

ORD-Eintrag
ord-1ea0799775a1465ab2ed108d61c68888
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169209B2

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