1,2-Dichloroethane → Ethyl1-Benzyl-3-((5-fluoropyridin-3-yl)methylcarbamoyl)-2-isopropyl-1H-indole-6-carboxylate

HRID 40069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40069
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]=2)[C:10]([C:22]([OH:24])=O)=[C:9]1[CH:25]([CH3:27])[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.[F:32][C:33]1[CH:34]=[C:35]([CH2:39][NH2:40])[CH:36]=[N:37][CH:38]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]=2)[C:10]([C:22](=[O:24])[NH:40][CH2:39][C:35]2[CH:36]=[N:37][CH:38]=[C:33]([F:32])[CH:34]=2)=[C:9]1[CH:25]([CH3:27])[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 111,2-DichloroethaneHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 597623601-Benzyl-6-(ethoxylcarbonyl)-2-isopropyl-1H-indole-3-carboxylic Acid2×

Produkt 1

HCID 59762375Ethyl1-Benzyl-3-((5-fluoropyridin-3-yl)methylcarbamoyl)-2-isopropyl-1H-indole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

Following General Procedure E, 1-benzyl-6-(ethoxylcarbonyl)-2-isopropyl-1H-indole-3-carboxylic acid (Compound 39, 93 mg, 0.254 mmol) in CH2Cl2 (6 ml) was added EDC (97 mg, 0.508 mmol) and DMAP (46 mg, 0.381mmol), followed by (5-fluoropyridin-3-yl)methanamine (81 mg, 0.63 mmol). The reaction was stirred at room temperature for 12 h, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→80% EtOAc-hexanes) to yield the title compound as a yellow solid.

Aufarbeitung

  1. washwashed with H2O, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (0→80% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0f95d269d60e400da2aafd597cc13adc
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524917B2

Notizen zur Reaktion

Wird geladen…