2,7-Diamino-9-fluorenone → HCID 10437549, compound

Participants

Reaction Steps

3-Methoxybenzenesulfonyl chloride (4.75 g, 23.0 mmol) in THF (40 mL) was treated with the product from Example 16A (5.05 g, 24 mmol) in THF (60 mL) and pyridine (60 mL) over 10 minutes. After an additional 30 minutes, the mixture was quenched with a mixture of 1.0M (pH 6) aqueous potassium phosphate buffer (30 mL) and brine (20 mL). The aqueous phase was separated and extracted with diethyl ether. The organic phases were combined, washed 1.0M (pH 6) aqueous potassium phosphate buffer (10 mL) and brine (10 mL), and the aqueous phase was extracted with diethyl ether. All the organic phases were combined, dried (Na2SO4), concentrated, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (ethyl acetate/CH2Cl2). The appropriate fractions were concentrated, dissolved in a small quantity of hot methanol and triturated with diethyl ether. The resulting precipitate was collected by filtration and washed with (10% methanol/diethyl ether) to provide the title compound as an orange powder (3.51 g). 1H HNMR (DMSO-d6) δ 10.55 (bs, 2H), 7.53 (d, J=8.5 Hz, 2H), 7.47 (t, J=8.0 Hz, 2H), 7.33 (d, J=7.6 Hz, 2H), 7.28-7.24 (m, 6H), 7.18 (dd, J=8.5, 2.1, 2H), 3.77 (s, 6H); MS calculated for (M+H): 550.0868; observed: 550.0848; IR 3232, 2971, 1719, 1599, 1466, 1256, 1155.

Provenance & Evidence