Potassium Phosphate, Tribasic → 9-tert-butyl-2-isobutyramido-3-methoxy-13-(2-thienyl)-5,6,9,10,11,12-hexahydro-8H-azepino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 250 mg of 3d, 110 mg of isobutyramide, 230 mg of K3PO4, 15 mg of Pd2 dba3 and 20 mg of di-tert-butyl(2′,4′,6′-triisopropyl-3,4,5,6-tetramethylbiphenyl-2-yl)phosphine in 3 ml of degassed tert-butanol was heated under nitrogen atmosphere for 16 hr at 100° C. The reaction mixture was cooled and diluted with 20 ml of water. The product was extracted into ethyl acetate. The extract was washed with water, dried, concentrated and the product was purified by chromatography over silica gel, using a gradient of heptane/ethyl acetate as eluent, to provide 120 mg of 3f. The sample was crystallized from ethyl acetate; MS-ESI: [M+1] 506.25. NMR (CDCl3) δ 1.18 (d, 6, isoC3H7), 1.58 (s, 9, tertC4H9), 1.89 (m, 2, CH2), 2.44 (m, 1, CH), 2.58 (t, 2, CH2), 3.01 (t, 2, CH2), 3.42 (t, 2, CH2), 3.86 (s, 3, OCH3), 4.50 (t, 2, CH2), 6.70 (s, 1 ArH) and 7.46 (bs, 1, ArH), 7.00, 7.18 and 7.38 (3×m, 3, thiophene-H), 8.08 (bs, 1, NH).

Provenance & Evidence