Cesium carbonate → 3-Chloro-N-{3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide

HRID 573634

Reaktionsgleichung

Reaktionsgleichung von HRID 573634
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[S:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[C:3]=12.[Cl:19][C:20]1[CH:21]=[C:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:19][C:20]1[CH:21]=[C:22]([S:26]([NH:29][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[S:8][CH:9]=[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=4)[C:3]=23)(=[O:27])=[O:28])[CH:23]=[CH:24][CH:25]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 5193773-ChlorobenzenesulfonamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 683237304-Chloro-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine

Produkt 1

HCID 683240753-Chloro-N-{3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamideAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 4-chloro-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine (Description 43) (100 mg, 0.363 mmol), 3-chlorobenzensulfonamide (90 mg, 0.471 mmol), palladium(II) acetate (8.14 mg, 0.036 mmol), xantphos (42.0 mg, 0.073 mmol), and Cs2CO3 (236 mg, 0.725 mmol) in 1,4-dioxane (3.6 mL) was degassed with nitrogen for 5 min. The mixture was heated at 150° C. for 45 min in a microwave and then poured into water (50 mL) and extracted with DCM (30 mL×4). The organic layers were combined, washed with brine (50 mL), dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with a gradient of 0-10% ethanol in toluene, followed by further purification by MDAP (basic conditions), to give the title compound (72 mg). LCMS (A) m/z: 431 [M+1]+, Rt 1.34 min (acidic).

Aufarbeitung

  1. customwas degassed with nitrogen for 5 min
  2. additionpoured into water (50 mL)
  3. extractionextracted with DCM (30 mL×4)
  4. washwashed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by chromatography on silica
  9. washeluting with a gradient of 0-10% ethanol in toluene
  10. customfollowed by further purification by MDAP (basic conditions)

Quellen und Nachweise

ORD-Eintrag
ord-2fa70b2e380f4c1eae69275cc2b6d71f
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029545B2

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