Sodium Iodide → HCID 86607901, compound

Participants

Reaction Steps

To 364 mg (0.673 mmol) of (3S,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (Example 47, Step 8) was added ethanol (6 mL), catalytic sodium iodide, potassium carbonate (112 mg, 0.812 mmol), and propargyl chloride (52 μL) and the resulting mixture was heated to reflux overnight. The solvent was then concentrated and the residue was dissolved in ethyl acetate. The organics were washed with saturated aqueous Na2CO3 (3×), dried over Na2SO4, concentrated, and then purified via column chromatography on silica gel eluting with 50% ethyl acetate/hexanes to give (3S,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-1-(prop-2-ynyl)piperidine-3-carboxamide (235 mg, 0.406 mmol, 60%) as a colorless solid. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 0.92-0.96 (m, 3H) 1.23-1.30 (m, 11H) 1.60-1.71 (m, 1H) 1.89-1.97 (m, 1H) 2.05-2.12 (m, 1H) 2.27-2.36 (m, 2H) 2.74 (s, 3H) 2.84-2.91 (m, 1H) 3.00 (ddd, J=12.06, 7.52, 4.17 Hz, 1H) 3.14 (dd, J=10.74, 2.15 Hz, 1H) 3.16-3.20 (m, 1H) 3.34 (dd, J=16.67, 2.53 Hz, 1H) 5.54 (s, 2H) 6.16 (d, J=7.58 Hz, 1H) 7.07-7.12 (m, 2H) 7.41 (s, 1H) 7.52-7.57 (m, 1H) 7.71 (ddd, J=8.46, 6.95, 1.26 Hz, 1H) 7.81-7.86 (m, 2H) 7.90 (d, J=7.58 Hz, 1H) 8.08 (d, J=8.59 Hz, 1H) 10.71 (s, 1H).

Provenance & Evidence