Triethylamine → 1-[4-(2,2,2-trifluoro-ethanesulfonylamino)-benzyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 342807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342807
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][C:16]1([CH3:21])[O:20][CH2:19][CH2:18][O:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(N(CC)CC)C.[F:37][C:38]([F:45])([F:44])[CH2:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([NH:29][S:40]([CH2:39][C:38]([F:45])([F:44])[F:37])(=[O:42])=[O:41])=[CH:27][CH:28]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][C:16]1([CH3:21])[O:20][CH2:19][CH2:18][O:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 675989771-(4-Amino-benzyl)-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic Acid Ethyl Ester

Produkt 1

HCID 675985121-[4-(2,2,2-trifluoro-ethanesulfonylamino)-benzyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic acid ethyl esterAusbeute 105,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of crude 1-(4-amino-benzyl)-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester (2 g, ≈5 mmol) in methylene chloride (25 ml) stirring at about -78° C. under nitrogen was added triethylamine (1.28 g, 1.76 ml, 12.7 mmol). The mixture was stirred for about two minutes, and 2,2,2-trifluoroethanesulfonyl chloride (2.03 g, 1.23 ml, 12.7 mmol) was added dropwise via syringe over about five minutes. The mixture was stirred at about -78° C. for about 45 minutes, then diluted with methylene chloride and water and warmed to room temperature. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo to an oil. The oil was taken up in methanol (30 ml) and triethylamine (1 ml) and stirred for about two hours at room temperature. The mixture was poured into half-saturated ammonium chloride and extracted into ethyl acetate. The ethyl acetate was washed with brine, dried over sodium sulfate, filtered, and evaporated to give the title compound (2.85 g) as a foam containing some impurities, which was reacted without further purification.

Aufarbeitung

  1. stirringThe mixture was stirred at about -78° C. for about 45 minutes
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo to an oil
  5. stirringtriethylamine (1 ml) and stirred for about two hours at room temperature
  6. additionThe mixture was poured into half-saturated ammonium chloride
  7. extractionextracted into ethyl acetate
  8. washThe ethyl acetate was washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6732481af2cc41d6a05c562a8b125088
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859044

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