Pyridine → HCID 22676787, compound

Participants

Reaction Conditions

Reaction Steps

Pyridine (0.18 mL, 174 mg, 2.2 mmol) and phosgene (1.9 M in toluene, 0.66 mL, 1.2 mmol) were added to a cooled (0° C.) and stirred solution of ethyl 5-amino-3-(4-tert-butylphenyl)-1-(3-methoxybenzyl)-1H-indole-2-carboxylate (Example 160, 500 mg, 1.1 mmol) in dichloromethane (10 mL). The reaction was warmed to rt and stirred for 3 h. The solution was concentrated in vacuo leaving crude Example 172. A portion (260 mg, 0.54 mmol) of the intermediate was dissolved in dichloromethane (10 mL) and then (cyclopropylmethyl)amine (0.13 mL, 108 mg, 1.5 mmol) was added. The reaction was stirred at rt for 16 h and then diluted with dichloromethane (100 mL). The solution was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Flash chromatography of the residue over silica gel using 3:1 hexane/ethyl acetate gave 160 mg (54%) of the desired product. The product had: 1H NMR (300 MHz, acetone-D6) δ 8.08 (d, 1 H), 7.09-7.45 (m, 7 H), 6.60-6.78 (m, 3 H), 6.33 (dd, 1 H), 5.76 (s, 2 H), 3.91 (q, 2 H), 3.68 (s, 3 H), 1.32 (s, 3 H), 0.87-0.96 (m, 1 H), 0.72 (t, 3 H), 0.31-0.41 (m, 2 H), 0.11-0.21 (m, 2 H).

Provenance & Evidence