N,N-Dimethylglycine → HCID 67263270, compound

Participants

Reaction Conditions

Reaction Steps

A procedure described in Syn. Lett. 1254, 2004 was followed. To solution of 2-amino-5-iodopyridine (220 mg, 1 mmol) in dimethyl formamide (2 mL) were added sequentially 3-mercaptobenzoic acid (185 mg, 1.2 mmol), CuI (50 mg), N,N-dimethylglycine (50 mg) and K3PO4 (1.06 g). The mixture was heated to 120° C. for 2 h, cooled to RT and water was added. The solid was filtered and the filtrate was treated with 1N HCl to adjust the solution to pH 4. The solid formed was collected by filtration, dissolved in 1N NaOH and the solution was filtered. The filtrate was purified by RP HPLC eluting with a mixture of methanol in water containing 0.1% TFA to obtain 3-(6-aminopyridin-3-ylthio)benzoic acid (84 mg, 34%). LC/MS; (M+H)+=247.

Provenance & Evidence