Reaktion #48918

Reaktionsgleichung

3-bromo-4,5-dichloropyridine

Sodium hydride

4-amino-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

DMSO

→

4-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

Lösungsmittel

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc
2. 2
   ExtraktionThe organic extract
3. 3
   Sonstigewas dried
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   Sonstigepurified by reverse-phase HPLC (20→100% MeCN/H2O)

Vorschrift

Sodium hydride (7 mg, 60%, 0.18 mmol) was added to a solution of 4-amino-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (77 mg, 0.28 mmol, Example 3, Step 1) and anhydrous DMSO (3 mL) under N2. After 10 min, 3-bromo-4,5-dichloropyridine (69 mg, 0.31 mmol) was added, and the reaction was stirred for 20 h, poured into brine, and extracted with EtOAc. The organic extract was dried, filtered, concentrated, and purified by reverse-phase HPLC (20→100% MeCN/H2O) to give 4-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.54 (s, 1H), 8.91 (s, 1H), 8.84 (s, 1H), 7.95 (d, 1H), 7.21 (d, 1H), 4.85 (m, 1H), 4.59 (s, 1H), 3.92 (s, 3H), 1.87-1.79 (m, 4H), 1.68-1.54 (m, 4H); MS (ESI): 464.7.

Quelle