1,2-Dimethoxyethane → 9-tert-butyl-3-methoxy-2-pyridin-3-yl-14-chloro-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 65 mg of 19e, 25 mg of 3-pyridine-boronic acid, 45 mg of K2CO3 and 12 mg of Pd(PPh3)4 in 3 ml of degassed 90% aq. dimethoxyethane was heated under a nitrogen atmosphere for 16 h at 90° C. The mixture was diluted with water, extracted with ethyl acetate, dried and concentrated. The residues were purified by chromatography over silica gel, using a gradient of heptane/ethyl acetate as eluent. The material thus obtained was triturated with pentane, to provide 45 mg of white crystalline 19f; Mp: 190-192° C. MS-ESI: [M+1] 464.17, 465.17 and 466.17. NMR (CDCl3) δ 1.58 (s, 3, tertC4H9), 1.62-1.77 (bm, 2, CH2), 1.80-2.05 (bm, 2, CH2), 2.60-2.77 (bm, 2, CH2), 2.970-3.18 (bm, 2, CH2), 3.50 bm, 1, CH), 3.76-3.92 (bm, 2, CH2), 3.86 (s, 3, OCH3), 4.50 (bm, 1, CH), 6.87 (s, 1, ArH), 8.20 (s, 1, ArH), 7.36, 7.89, 8.57, 8.83 (4×m, 4, pyridine-H).

Provenance & Evidence