Hydrochloric Acid → 6-chloro-5-[4-(pyrrolidin-2-yl)phenyl]-1H-indole-3-carboxylic acid

HRID 338425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338425
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][C:27]=2[Cl:28])[NH:24][CH:23]=[C:22]3[C:29]([OH:31])=[O:30])=[CH:15][CH:14]=1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[Cl:28][C:27]1[CH:26]=[C:25]2[C:21]([C:22]([C:29]([OH:31])=[O:30])=[CH:23][NH:24]2)=[CH:20][C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:18][CH:17]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 866987595-{4-[1-(tert-butoxycarbonyl)pyrrolidin-2-yl]phenyl}-6-chloro-1H-indole-3-carboxylic acid

Produkt 1

HCID 866987606-chloro-5-[4-(pyrrolidin-2-yl)phenyl]-1H-indole-3-carboxylic acidAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a suspension of 5-{4-[1-(tert-butoxycarbonyl)pyrrolidin-2-yl]phenyl}-6-chloro-1H-indole-3-carboxylic acid (140 mg, 0.318 mmol) in ethyl acetate (10 mL) was added hydrogen chloride in ethyl acetate (4N HCl in EtOAc, 10 mL) under nitrogen. The suspension was stirred for 4.5 hours at room temperature. The mixture was concentrated to afford the desired product (100 mg, 83.5% yield). MS (ES+) 341 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.10 (s, 1H), 7.95 (s, 1H), 7.66 (s, 1H), 7.62 (d, 2H), 7.52 (d, 2H), 4.60 (s, 1H), 3.35 (s, 4H), 2.49 (m, 2H).

Aufarbeitung

  1. concentrationThe mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-751b8a4db5aa4f2ab93c82d558651a6a
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

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