3-Butyn-1-OL → HCID 10178842, compound

Participants

Reaction Steps

A solution of N-(4-chlorobenzyl)-6-iodo-1-methyl-4-oxo-1,4-dihydro-3-cinnolinecarboxamide [Example 1] (0.12 g), copper iodide (0.020 g), Pd(PPh3)2Cl2 (0.0067 g) and 3-butyn-1-ol (0.030 mL) in 10 mL diethylamine is stirred at room temperature for 18 h. The reaction is partitioned between ethyl acetate and H2O. The aqueous layer is extracted 3× with ethyl acetate. The organics are combined, dried over Na2SO4, filtered and concentrated. The residue is dissolved in CH2Cl2/MeOH and adsorbed onto silica. Purification by Biotage Flash 40S (eluent CH2Cl2 (1L), 1% MeOH/CH2Cl2 (1L), 2% MeOH/CH2Cl2 (1L), 3% MeOH/CH2Cl2 (1L)) affords the desired product which is recrystallized with CH2Cl2/hexanes (0.059 g, 56%). Physical characteristics are as follows: m.p. 227-229° C.; 1H NMR (300 MHz, DMSO-d6) δ9.90, 8.18, 7.93, 7.40, 4.97, 4.55, 4.24, 3.62, 2.62; IR (drift) 3238, 3176, 1671, 1614, 1594, 1551, 1493, 1470, 1411, 1321, 1281, 1045, 825, 808, 733 cm−1; MS (ESI) m/z 396.0 (M+H)+; HRMS (FAB) calcd for C21H18ClN3O3+H1 396.1115, found 396.1114.

Provenance & Evidence