Pyrrolidine → HCID 22641503, compound

Participants

Reaction Steps

A suspension of 98.5 mg (0.25 mmol) of 7-(6-chloro-pyridin-3-ylmethoxy)-2-methyl-4-pyrrolidin-1-yl-quinoline hydrochloride, product of example 56, 16 mg (0.03 mmol) of BINAP, 2.8 mg (0.01 mmol) of Pd(II) acetate, and 99 mg (1 mmol) of sodium tert-butylate in toluene (4.5 ml) was treated at RT with 36 mg (0.5 mmol) of pyrrolidine and then heated at reflux under an argon atmosphere for 4 h. The reaction mixture was cooled to RT, diluted with methylene chloride (10 ml), and then filtered. The filtrate was concentrated in vacuo, the residue triturated with ether, filtered off by suction and dried in a high vacuum to give 88 mg (84%) of the 2-methyl-4-pyrrolidin-1-yl-7-(6-pyrrolidin-1-yl-pyridin-3-ylmethoxy)-quinoline as a white solid. ISP mass spectrum, m/e: 389.3 (M+1 calculated for C24H28N4O: 389).

Provenance & Evidence