Reaktion #46932

Reaktionsgleichung

mixture

5-(4-chloro-phenyl)-4-iodo-2-methyl-1-(4-sulfamoyl-phenyl)-1H-pyrrole-3-carboxylic Acid Ethyl Ester

4-(hydroxymethyl)phenylboronic acid

Cs2CO3

→

5-(4-chloro-phenyl)-4-(4-hydroxymethyl-phenyl)-2-methyl-1-(4-sulfamoyl-phenyl)-1H-pyrrole-3-carboxylic Acid Ethyl Ester

Lösungsmittel

ethanol

Et2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through diatomaceous earth with Et2O
2. 2
   Waschenrinse
3. 3
   WaschenThe filtrate was washed with 1 M pH 7 potassium phosphate buffer
4. 4
   Trocknendried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   Sonstigethe residue chromatographed on an Alltech silica column (average pore size 60 Å, particle size 50 μM) (30→10% hexanes/Et2O)
8. 8
   Sonstigeto provide a white foam

Vorschrift

To a mixture of Example 96 (33 mg, 0.060 mmol), 4-(hydroxymethyl)phenylboronic acid (12 mg, 0.080 mmol), palladium acetate (2.2 mg, 0.010 mmol) suspended in ethanol (0.50 mL) was added 1 M aqueous Cs2CO3 (0.080 mL, 0.080 mmol), and heated in a microwave (Personal Chemistry: Emrys Creator) at 110° C. for 15 minutes. The mixture was diluted with Et2O (2 mL), stirred thoroughly, filtered through diatomaceous earth with Et2O rinse. The filtrate was washed with 1 M pH 7 potassium phosphate buffer, dried (Na2SO4), filtered and concentrated under reduced pressure and the residue chromatographed on an Alltech silica column (average pore size 60 Å, particle size 50 μM) (30→10% hexanes/Et2O) to provide a white foam. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.81 (d, 2H), 7.49 (d, 2H), 7.48 (bs, 2H), 7.14 (d, 2H), 7.14 (d, 2H), 7.06 (d, 2H), 6.95 (d, 2H), 5.10 (t, 1H), 4.45 (d, 2H), 4.02 (q, 2H), 2.32 (s, 3H), 1.0 (t, 3H); MS (ESI) m/z m/z 525/527.

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