4-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid tert-butyl ester → 4-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid

HRID 1630796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1630796
C([O:5][C:6](=[O:32])[C:7]1[CH:12]=[CH:11][C:10]([C:13]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([C:24]#[N:25])=[CH:21][CH:22]=3)[CH:17]=[C:16]2[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[O:14])=[CH:9][CH:8]=1)(C)(C)C>C(O)(C(F)(F)F)=O>[C:24]([C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[N:15]([C:13]([C:10]1[CH:9]=[CH:8][C:7]([C:6]([OH:32])=[O:5])=[CH:12][CH:11]=1)=[O:14])[C:16]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)=[CH:17]2)#[N:25]

Komponenten

3

Edukt 1

HCID 582157224-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid tert-butyl ester

Produkt 1

HCID 582157044-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

4-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid tert-butyl ester (100 mg) is dissolved in TFA (3 mL) and stirred at ambient temperature for 1 h. The solvent is removed in vacuo and the residue is triturated with diethyl ether twice. The residue is purified by reverse phase HPLC with Sunfire C18 and a gradient of acetonitrile in 0.1% aqueous TFA to afford 4-(5-cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm (TFA salt) 7.24 (s, 1H), 7.28 (dd, J=7.9, 4.9 Hz, 1H), 7.73-7.77 (m, 4H), 7.81 (dt, J=8.1, 1.9, 1.8 Hz, 1H), 7.87-7.91 (m, 2H), 8.32 (t, J=1.1 Hz, 1H), 8.41 (dd, J=4.9, 1.6 Hz, 1H), 8.63-8.65 (m, 1H), 13.40 (br. s., 1H). HRMS (ESI) m/z 366.0868 [(M+H)+ Calcd for C22H14N3O3: 366.0879].

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. customthe residue is triturated with diethyl ether twice
  3. customThe residue is purified by reverse phase HPLC with Sunfire C18

Quellen und Nachweise

ORD-Eintrag
ord-dbaec33b57e143c991ba5faadbc3fbaf
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791141B2

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