2-Amino-5-methylpyridine → 2-Methyl-N-(5-methylpyridin-2-yl)-4-(4-(methylsulfonyl)-phenoxy)-benzofuran-6-carboxamide

HRID 1643725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643725
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Al](Cl)(C)C.[CH3:13][C:14]1[O:15][C:16]2[CH:22]=[C:21]([C:23](OCC)=[O:24])[CH:20]=[C:19]([O:28][C:29]3[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=3)[C:17]=2[CH:18]=1>ClCCCl>[CH3:13][C:14]1[O:15][C:16]2[CH:22]=[C:21]([C:23]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=3)=[O:24])[CH:20]=[C:19]([O:28][C:29]3[CH:30]=[CH:31][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:33][CH:34]=3)[C:17]=2[CH:18]=1

Komponenten

5

Edukt 3

HCID 153482-Amino-5-methylpyridineHCID 79147ChlorodimethylaluminumHCID 59560179Ethyl 2-methyl-4-(4-(methylsulfonyl)phenoxy)benzofuran-6-carboxylate

Produkt 1

HCID 667558692-Methyl-N-(5-methylpyridin-2-yl)-4-(4-(methylsulfonyl)-phenoxy)-benzofuran-6-carboxamideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

2-Amino-5-methyl pyridine (289 mg, 2.67 mmol) was dissolved in DCE (10 mL) at 0° C., then Al(CH3)2Cl (2.67 mL, 1M in hexanes) was added drop wise. After the addition, the ice-bath was removed, and the mixture was stirred for 30 min at room temperature. Ethyl 2-methyl-4-[4-(methylsulfonyl)phenoxy]-1-benzofuran-6-carboxylate (100 mg, 0.267 mmol) was added and the stirring was continued for 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 crude product was purified by gradient silica gel chromatography using CHCl3/MeOH (100/0 to 98/2) to give the title compound (100 mg, 86%) as a white solid. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 2.32 (s, 3 H) 2.48 (s, 3 H) 3.07 (s, 3H) 6.24 (s, 1 H) 7.08-7.16 (m, 2 H) 7.48 (d, J=1.32 Hz, 1 H) 7.57 (dd, J=8.29, 2.35 Hz, 1 H) 7.81-7.97 (m, 3 H) 8.12 (d, J=2.35 Hz, 1 H) 8.25 (d, J=8.29 Hz, 1 H) 8.44 (s, 1 H). LCMS for C23H20N2O5S m/z 437.4 (M+H)+.

Aufarbeitung

  1. additionAfter the addition
  2. customthe ice-bath was removed
  3. waitthe stirring was continued for 14 h
  4. customThe reaction was quenched with potassium sodium tartrate tetrahydrate (20% w/w) cautiously
  5. extractionThe product was extracted with CHCl3
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. customThe crude product was purified by gradient silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c5fec9fdcde648f1bd349d66463165b7
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119624B2

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