3-Chlorobenzenesulphonyl chloride → 3-Chloro-N-{2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide

HRID 573688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573688
[CH3:1][C:2]1[S:13][C:5]2[N:6]=[C:7]([O:11][CH3:12])[CH:8]=[C:9]([NH2:10])[C:4]=2[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:32][C:33]1[CH:34]=[C:35]([S:39](Cl)(=[O:41])=[O:40])[CH:36]=[CH:37][CH:38]=1>C1COCC1>[Cl:32][C:33]1[CH:34]=[C:35]([S:39]([NH:10][C:9]2[CH:8]=[C:7]([O:11][CH3:12])[N:6]=[C:5]3[S:13][C:2]([CH3:1])=[C:3]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=4)[C:4]=23)(=[O:41])=[O:40])[CH:36]=[CH:37][CH:38]=1

Komponenten

5

Edukt 3

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 683241312-Methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine

Produkt 1

HCID 683237633-Chloro-N-{2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamideAusbeute 42,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine (Description 37) (16.5 mg, 0.055 mmol) in THF (0.5 mL) at −78° C. under a nitrogen atmosphere was added LiHMDS (1M solution in THF) (0.055 mL, 0.055 mmol). The solution was stirred at −78° C. for ca. 10 min before the addition of 3-chlorobenzenesulfonyl chloride (7.73 μL, 0.055 mmol). The reaction mixture was then warmed to RT under a nitrogen atmosphere overnight and was then partitioned between water and ethyl acetate (ca. 10 mL each). The aqueous layer was separated and re-extracted with ethyl acetate (ca. 10 mL). The combined organic layer was passed through phase separator and the solvent concentrated in vacuo. The residue was purified by MDAP (acidic conditions), to give the title compound (11 mg). LCMS (A) m/z: 475 [M+1]+, Rt 1.63 min (acidic).

Aufarbeitung

  1. customwas then partitioned between water and ethyl acetate (ca. 10 mL each)
  2. customThe aqueous layer was separated
  3. extractionre-extracted with ethyl acetate (ca. 10 mL)
  4. concentrationthe solvent concentrated in vacuo
  5. customThe residue was purified by MDAP (acidic conditions)

Quellen und Nachweise

ORD-Eintrag
ord-349f63cb3f2746fd804b2b70ef5dda9a
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029545B2

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