Boron trifluoride etherate → N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[3,4-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide

HRID 2393134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393134
[Cl:1][C:2]1[C:3]([CH3:37])=[N:4][O:5][C:6]=1[N:7]([CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH:20](O)[C:21]1[CH:26]=[CH:25][C:24]2[O:27][CH2:28][O:29][C:23]=2[CH:22]=1)(=[O:10])=[O:9].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[C:3]([CH3:37])=[N:4][O:5][C:6]=1[N:7]([CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]2[O:27][CH2:28][O:29][C:23]=2[CH:22]=1)(=[O:9])=[O:10]

Komponenten

6

Edukt 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 54238526N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-(alpha-hydroxy-3,4-(methylenedioxy) benzyl]-thieno [2,3-b]pyridine-3-sulfonamide

Produkt 1

HCID 18614044N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[3,4-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamideAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-(α-hydroxy-3,4-(methylenedioxy)benzyl]-thieno[2,3-b]pyridine-3-sulfonamide (0.10 g, 0.18 mmoles)[see Example 4(B)] and triethylsilane (0.29 ml, 1.8 mmoles) in CH2Cl2 (2 ml) was added boron trifluoride etherate (0.10 ml, 0.81 mmoles). The orange-brown solution was stirred 2 hours at ambient temperature then diluted with EtOAc (50 ml) and washed with H2O (75 ml). The organic layer was dried (MgSO4), filtered and concentrated to collect an orange oil. Flash chromatography (40% EtOAc/hexanes) provided 66 mg (66%) of the title compound as a yellow oil.

Aufarbeitung

  1. washwashed with H2O (75 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto collect an orange oil

Quellen und Nachweise

ORD-Eintrag
ord-5a75cc8faa934d89ad4f63f1534e09ed
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05804585

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