Reaktion #48958

Reaktionsgleichung

TMSCHN2

6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanoic acid

6-(4-(3,5-Dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanoic acid

methanol

→

methyl 6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanoate

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthe reaction was concentrated
2. 2
   Sonstigepurified by silica gel chromatography (4:1→1:4; hexanes:ethyl acetate)

Vorschrift

A solution of TMSCHN2 (0.75 mL, 2M Et2O, 1.5 mmol) was added to a solution of 6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanoic acid (115 mg, 0.25 mmol, Example 44), methanol (1 mL), and toluene (8 mL). After 10 min, the reaction was concentrated and purified by silica gel chromatography (4:1→1:4; hexanes:ethyl acetate) to give methyl 6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanoate: 1H NMR (400 MHz, DMSO-d6): δ 9.50 (s, 1H), 8.81 (s, 2H), 7.94 (d, 1H), 7.20 (d, 1H), 4.63 (s, 1H), 3.97 (t, 2H), 3.91 (s, 3H), 3.56 (s, 3H), 2.31 (t, 2H), 1.67 (m, 2H), 1.57 (m, 2H), 1.46 (m, 2H); MS (ESI): 480.9.

Quelle