Trifluoroacetic acid → 5-(2-Amino-ethyl)-2-(5-trifluoromethyl-pyridin-2-yloxy)benzonitrile

HRID 474735Notes

Reaction equation

C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=2)=[C:12]([C:27]#[N:28])[CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl.C([O-])(O)=O.[Na+]>[NH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][N:18]=2)=[C:12]([CH:11]=1)[C:27]#[N:28]

Participants

Conditions

Temperature: 0 °C

Procedure

Entire reaction was performed under argon atmosphere using syringe septa technique. {2-[3-cyano-4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (0.425 mmol, 1 eq) was dissolved in dichloromethane (1.5 ml) and stirred at 0° C. for 5 min. TFA (2.213 mmol, 5 eq) was added and stirring was continued for 2 hours. Reaction mixture was diluted with 10 ml NaHCO3 (sat.) and extraction with DCM (3×20 ml) followed. Organic layers were combined and evaporated in vacuo to give 5-(2-amino-ethyl)-2-(5-trifluoromethyl-pyridin-2-yloxy)benzonitrile (0.391 mmol, yield=92%, purity=80%). [M+H]+=308.29 1H NMR (300 MHz, CDCl3) δ/ppm 2.79 (br. s., 2H), 2.94-3.07 (m, 2H), 7.21 (br. s., 2H), 7.49 (d, J=8.9 Hz, 1H), 7.54 (br. s., 1H), 7.90-8.05 (m, 1H), 8.38 (br. s., 1H)

Workup

customEntire reaction
stirringstirring
waitwas continued for 2 hours
customReaction mixture
customevaporated in vacuo

Sources & evidence

ORD record: ord-a78e5a5ec66447b08bf4587ca494eb81
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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