Sodium Carbonate → N-(3-Chloroimidazo[1,2-a]pyridin-2-yl)-N-(4-fluoro-3-trifluoromethylbenzyl)-6-morpholin-4-yl-pyridine-3-sulfonamide

HRID 2178566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2178566
[Cl:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[NH:11][S:12]([C:15]1[CH:16]=[N:17][C:18]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:19][CH:20]=1)(=[O:14])=[O:13].C([O-])([O-])=O.[Na+].[Na+].[F:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][C:35]=1[C:42]([F:45])([F:44])[F:43]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[N:11]([CH2:38][C:37]1[CH:40]=[CH:41][C:34]([F:33])=[C:35]([C:42]([F:45])([F:43])[F:44])[CH:36]=1)[S:12]([C:15]1[CH:16]=[N:17][C:18]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:19][CH:20]=1)(=[O:14])=[O:13]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27375774-Fluoro-3-(trifluoromethyl)benzyl bromideHCID 67953931N-(3-Chloroimidazo[1,2-a]pyridin-2-yl)-6-morpholin-4-yl-pyridine-3-sulfonamide

Produkt 1

HCID 67954012N-(3-Chloroimidazo[1,2-a]pyridin-2-yl)-N-(4-fluoro-3-trifluoromethylbenzyl)-6-morpholin-4-yl-pyridine-3-sulfonamideAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of compound 11-E (0.030 g, 0.049 mmol) in DMF (1 mL) was added Na2CO3 (0.015 g, 0.15 mmol) and 4-fluoro-3-trifluoromethylbenzyl bromide (0.014 g, 0.053 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water, and dried over sodium sulfate. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography, eluting with a hexanes-EtOAc gradient to give Compound 90 as a yellow solid (0.008 g, 29%); MS m/z (M+H+) 570.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by flash column chromatography
  5. washeluting with a hexanes-EtOAc gradient

Quellen und Nachweise

ORD-Eintrag
ord-ecc145539cc2453fa25dac8a9ed809a3
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067935B2

Notizen zur Reaktion

Wird geladen…