6-CYANO-4-CHROMANONE synthesis
- Product Name:6-CYANO-4-CHROMANONE
- CAS Number:214759-65-6
- Molecular formula:C10H7NO2
- Molecular Weight:173.17
557-21-1
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Yield:214759-65-6 62%
Reaction Conditions:
with tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide at 110; for 12 h;Inert atmosphere;
Steps:
(4R)-4-aminochromane-7-carbonitrile hydrochloride (81)
To a solution of 82 (10.5 g, 46.2 mmol) in dry DMF (100 mL) was added Zn(CN)2 (6.50 g, 116mmol) and Pd(PPh3)4 (2.5 g, 23% w/w%) under N2. Following addition, the system was purgedwith N2 three times. The reaction was heated to 110 °C and stirred overnight. The reaction wasmonitored by TLC and LCMS. The reaction was cooled to room temp and filtered through a padof Celite. The filtrate was poured into water and extracted with EtOAc before the organic layerswere washed with water, brine, dried over Na2SO4, concentrated and purified by FCC to give 83(5.01 g, 62%) as pale-yellow solid which was used directly for the next step.
References:
Le?niak, Robert K.;Nichols, R. Jeremy;Schonemann, Marcus;Zhao, Jing;Gajera, Chandresh R.;Fitch, William L.;Lam, Grace;Nguyen, Khanh C.;Smith, Mark;Montine, Thomas J. [European Journal of Medicinal Chemistry,2022,vol. 229,art. no. 114080] Location in patent:supporting information
