o-Fluorobenzaldehyde → HCID 66614832, compound

Participants

Reaction Steps

In a flask, dichloromethane (5 mL) and acetic acid (3 drops) was added to methyl 5-(thiomorpholine-2-carboxamido)-1H-indazole-3-carboxylate (0.320 g, 1 mmol) and 2-fluorobenzaldehyde (0.248 g, 2 mmol). The reaction was stirred for 15 minutes. Sodium triacetoxyborohydride (0.636 g, 3 mmol) was added in one portion. The reaction was stirred for an additional 16 hours. Saturated sodium bicarbarbonate (20 mL) was added. The reaction was stirred for an additional 5 minutes and was extracted with dichloromethane (30×1 mL). The extracts were combined, dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by flash column chromatography to give 250 mg product. LC-MS: 429.1.2 [M+H].

Provenance & Evidence