Sodium Carbonate → HCID 86722502, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of Compound 6 (30 g, 52 mmol) in anhydrous 1,4-dioxane (300 mL), POCl3 (30.6 g, 18.6 mL, 200 mmol) was added slowly with water bath cooling. The resulting mixture was then maintained at 100° C. After cooling to room temperature, the mixture was poured into ice (ca. 300 g) and neutralized with Na2CO3, followed by extraction with CH2Cl2 (2×300 mL). The organic phase was then washed with brine, dried over Na2SO4 and concentrated in vacuo. To the mixture, acetonitrile (300 mL) was added and stirred, then filtered. The solid was collected and recrystallized in CH2Cl2/hexane to afford a white solid (18.9 g). The filtrant was purified by flash chromatography (SiO2, 100% hexanes to 9:1 to 4:1-hexanes/ethyl acetate). The main fraction was collected and concentrated to give additional product, white solid (5.17 g). Total amount is 24.1 g (86%): confirmed by LCMS (APCI): calculated for C32H21BrN4 (M+): 541; Found: 541.

Provenance & Evidence