Benzenesulfonyl chloride → HCID 59508100, Verbindung

HRID 1958650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1958650
[CH3:1][O:2][C:3]1[C:8]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(C(C)C)CC)(C)C.[C:33]1([S:39](Cl)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[C:33]1([S:39]([N:21]2[CH2:22][CH2:23][CH:18]([C:17]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[NH:10][C:9]=3[C:8]3[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=3)[CH2:19][CH2:20]2)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Komponenten

5

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59508043HCID 59508043, Verbindung

Produkt 1

HCID 59508100HCID 59508100, VerbindungAusbeute 24,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-methoxy-pyridin-3-yl)-3-piperidin-4-yl-1H-indole (0.12 g, 0.39 mmol) in dichloromethane (10 ml) and diisopropylethylamine (0.20 ml, 1.17 mmol) was added phenylsulfonyl chloride (52 μl, 0.41 mmol). The reaction was stirred at room temperature for 4 h and quenched by adding water. The organic layer was separated, washed with aqueous sodium hydroxide, brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by a flash chromatography (SiO2, 30% EtOAc in hexane) to give the desired product as a white solid (0.042 g, 24%); M.p.=231-234° C.; 400 MHz 1H NMR (DMSO-d6) δ: 11.00 (s, 1H), 8.20 (dd, J1=0.8 Hz, J2=4.8 Hz, 1H), 7.77 (m, 3H), 7.66 (m, 3H), 7.29 (m, 2H), 7.07 (m, 2H), 6.92 (m, 1H), 3.84 (m, 5H), 2.56 (m, 1H), 2.42 (m, 2H), 2.00 (m, 2H), 1.66 (m, 2H); LCMS: 448.69 [M+H].

Aufarbeitung

  1. customquenched
  2. additionby adding water
  3. customThe organic layer was separated
  4. washwashed with aqueous sodium hydroxide, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by a flash chromatography (SiO2, 30% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-581dca729dd74d889285362bdb05744e
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410144B2

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