Pyridine → ethyl 7-{[(4-chlorobutyl)sulfonyl]amino}-3-ethyl-1H-indole-5-carboxylate

HRID 852616

Reaktionsgleichung

Reaktionsgleichung von HRID 852616
[NH2:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:11][CH3:12].N1C=CC=CC=1.[Cl:24][CH2:25][CH2:26][CH2:27][CH2:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[Cl:24][CH2:25][CH2:26][CH2:27][CH2:28][S:29]([NH:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:11][CH3:12])(=[O:31])=[O:30]

Komponenten

7

Edukt 3

HCID 1049PyridineHCID 742124-Chlorobutane-1-sulphonyl chlorideHCID 69356544ethyl 7-amino-3-ethyl-1H-indole-5-carboxylate

Produkt 1

HCID 69357263ethyl 7-{[(4-chlorobutyl)sulfonyl]amino}-3-ethyl-1H-indole-5-carboxylateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of ethyl 7-amino-3-ethyl-1H-indole-5-carboxylate (D222) (150 mg, 0.65 mmol, 1 equiv) in CH2Cl2 (10 ml) at room temperature were added pyridine (115 μl, 1.42 mmol, 2.2 equiv), 4-chloro-1-butanesulfonyl chloride (D20) (259 mg, 1.36 mmol, 2.1 equiv) and DMAP (8 mg, 0.065 mmol, 0.1 equiv) and the resulting mixture was stirred for 1 h then diluted with AcOEt and washed with a 2N aqueous HCl solution and brine, then dried over MgSO4 and concentrated in vacuo to give ethyl 7-{[(4-chlorobutyl)sulfonyl]amino}-3-ethyl-1H-indole-5-carboxylate (D242) (230 mg, 92%) as a purple oil which was used in the next step without further purification. [M+H]+=387.3, RT=3.35 min.

Aufarbeitung

  1. washwashed with a 2N aqueous HCl solution and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eaf63b513a3b4c9e9eba91478c58fca4
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253198B2

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