1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66599102, compound

To a suspension of 1H-indole-7-carboxylic acid (510.9 mg, 2.85 mmol, commercially available from e.g. Maybridge, Apollo or Fluorochem) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide (443 mg, 2.85 mmol) in Dichloromethane (15 ml) stirred under argon at room temp was added solid 1-H-1,2,3-benzotriazol-1-ol (43.7 mg, 0.285 mmol) in dichloromethane (15 ml). The reaction mixture was stirred at RT for 1 hr. Solid t-butyl carbazate (571 mg, 4.28 mmol) was added and the reaction mixture stirred at room temp for 18 hr. The reaction mixture was partitioned between dichloromethane (˜50 ml) and saturated sodium bicarbonate solution (˜25 ml). The aqueous phase was extracted with dichloromethane (2×25 ml) and the combined organic extracts washed with saturated sodium bicarbonate solution (˜25 ml), dried over sodium sulphate and evaporated in vacuo to give the crude product as a yellow gum. The residue was purified via Biotage (1:1 Hex/EtOAc; 25+M Biotage column) to afforded the required product as a white foam in 360.0 mg.

1. stirringthe reaction mixture stirred at room temp for 18 hr
2. customThe reaction mixture was partitioned between dichloromethane (˜50 ml) and saturated sodium bicarbonate solution (˜25 ml)
3. extractionThe aqueous phase was extracted with dichloromethane (2×25 ml)
4. washthe combined organic extracts washed with saturated sodium bicarbonate solution (˜25 ml)
5. dry with materialdried over sodium sulphate
6. customevaporated in vacuo
7. customto give the crude product as a yellow gum
8. customThe residue was purified via Biotage (1:1 Hex/EtOAc; 25+M Biotage column)

ORD record

ord-18a52493178949399d056faddb1c44e7

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501946B2