2-Amino-5-methylpyridine → N2,N2-Dimethyl-N6-(5-methylpyridin-2-yl)-4-(4-(methylsulfonyl)-phenoxy)-benzofuran-2,6-dicarboxamide

HRID 1177276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177276
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Al](Cl)(C)C.[CH3:13][N:14]([CH3:42])[C:15]([C:17]1[O:18][C:19]2[CH:25]=[C:24]([C:26](OCC)=[O:27])[CH:23]=[C:22]([O:31][C:32]3[CH:37]=[CH:36][C:35]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:34][CH:33]=3)[C:20]=2[CH:21]=1)=[O:16]>ClCCCl>[CH3:13][N:14]([CH3:42])[C:15]([C:17]1[O:18][C:19]2[CH:25]=[C:24]([C:26]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=3)=[O:27])[CH:23]=[C:22]([O:31][C:32]3[CH:37]=[CH:36][C:35]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:34][CH:33]=3)[C:20]=2[CH:21]=1)=[O:16]

Komponenten

5

Edukt 3

HCID 153482-Amino-5-methylpyridineHCID 79147ChlorodimethylaluminumHCID 66755872Ethyl 2-(dimethylcarbamoyl)-4-(4-(methylsulfonyl)phenoxy)-benzofuran-6-carboxylate

Produkt 1

HCID 66755862N2,N2-Dimethyl-N6-(5-methylpyridin-2-yl)-4-(4-(methylsulfonyl)-phenoxy)-benzofuran-2,6-dicarboxamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

2-Amino-5-methylpyridine (226 mg, 2.09 mmol) was dissolved in DCE (10 mL) at 0° C., and Al(CH3)2Cl (2.09 mL, 1M in hexanes) was then added drop-wise. After stirring the mixture at room temperature for 30 minutes, ethyl 2-(dimethylcarbamoyl)-4-(4-(methylsulfonyl)phenoxy)-benzofuran-6-carboxylate (90 mg, 0.21 mmol) was then added and the stirring was continued for another 14 h. The reaction was quenched with potassium sodium tartrate tetrahydrate (20% w/w) cautiously. The product was extracted with CHCl3, washed with brine, and dried over MgSO4. The product was purified by reverse phase HPLC to give the title compound (61 mg, 61%) as a white solid. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 2.32 (s, 3 H) 3.08 (s, 3 H) 3.15 (s, 3 H) 3.34 (s, 3 H) 7.12-7.18 (m, 2 H) 7.19 (s, 1 H) 7.52 (s, 1 H) 7.58 (dd, J=8.48, 2.26 Hz, 1 H) 7.87-7.98 (m, 2 H) 7.99 (s, 1 H) 8.11 (s, 1 H) 8.24 (d, J=8.48 Hz, 1 H) 8.64 (s, 1 H). LCMS m/z 494.0 (M+H)+.

Aufarbeitung

  1. waitthe stirring was continued for another 14 h
  2. customThe reaction was quenched with potassium sodium tartrate tetrahydrate (20% w/w) cautiously
  3. extractionThe product was extracted with CHCl3
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe product was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-805b096c90b04902b7fe17ae26b6886a
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842713B2

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