5-ACETAMIDOINDOLE

General procedure: General procedure (10): To a solution of aminoindole (1.0 equiv) and triethylamine (3.6 equiv) in dichloromethane (10 ml_ for 1.182 mmol of starting material), acetyl chloride (1.2 equiv) was added. The reaction was stirred at room temperature for 3 h. The mixture was poured into water and extracted with dichloromethane 3 times. The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuo. Purification by flash silica gel column chromatography afforded the indole-acetamide product. Intermediate 17 A/-(1/-/-indol-5-yl)acetamide Intermediate 17 (177 mg, 1.016 mmol) was prepared as a clear oil from Intermediate 16 (156 mg, 1.182 mmol) according to general procedure (10) using 7:3 hexane/ethyl acetate as the eluent for flash silica gel column chromatography. Yield: 85percent. To a solution of intermediate 16 (156 mg, 1.182 mmol, 1.0 equiv) and triethylamine (591 μL, 429 mg, 4.240 mmol, 3.6 equiv) in DCM (10 mL), acetyl chloride (101 μL, 111 mg, 1.418 mmol, 1.2 equiv) was added. The reaction was stirred at room temperature for 3 h. The mixture was poured into water and extracted with dichloromethane 3 times. The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuo. Purification by flash silica gel column chromatography (7:3 hexane/ethyl acetate) afforded intermediate 7g as a clear oil (177 mg, 1.016 mmol). Yield: 85percent.

Molecular Weight:174.20
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:174.079312947
Monoisotopic Mass:174.079312947
Topological Polar Surface Area:44.9
Heavy Atom Count:13
Complexity:205
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes