반응 #48921

반응 방정식

KH2PO4

Sodium hydride

4-amino-8-(cyclopentyloxy)-3-fluoro-7-methoxy-2H-chromen-2-one

3,4,5-trichloropyridine

→

8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-3-fluoro-7-methoxy-2H-chromen-2-one

용매

DMSO

반응 조건

후처리

1. 1
   workup.WAIT70° C. for 2 h
2. 2
   온도to cool to rt
3. 3
   추출extracted with ethyl acetate (40 mL×2)
4. 4
   기타The combined extracts were dried
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타purified by silica gel chromatography (7:3→0:1; hexanes:ethyl acetate)

실험 절차

Sodium hydride (40 mg, 60%, 1.0 mmol) was added to a solution of 4-amino-8-(cyclopentyloxy)-3-fluoro-7-methoxy-2H-chromen-2-one (95 mg, 0.32 mmol), 3,4,5-trichloropyridine (118 mg, 0.65 mmol), and DMSO (3 mL) at rt under N2. After 1.5 h, the reaction was heated at 50° C. for 2 h and then 70° C. for 2 h. The reaction was allowed to cool to rt, poured into 1M KH2PO4 (30 mL) and extracted with ethyl acetate (40 mL×2). The combined extracts were dried, filtered, concentrated, and purified by silica gel chromatography (7:3→0:1; hexanes:ethyl acetate) to give 8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-3-fluoro-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.36 (s, 1H), 8.70 (s, 2H), 7.90 (d, 1H), 7.25 (d, 1H), 4.84 (m, 1H), 3.90 (s, 3H), 1.90-1.45 (m, 8H); MS (ESI): 438.8.

출처