Trifluoroacetic acid → 2-[3-Bromo-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethylamine

HRID 705984Notes

Reaction equation

HRID 705984 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[C:11]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl.C([O-])(O)=O.[Na+]>[Br:16][C:12]1[C:11]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][N:19]=2)=[C:10]([CH2:9][CH2:8][NH2:7])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67776337{2-[3-Bromo-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 677761282-[3-Bromo-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethylamineYield 99.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

{2-[3-bromo-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (1.3 g, 2.818 mmol) was dissolved in dichloromethane (10 ml) and stirred at 0° C. for 5 min. TFA (1.08 ml, 14.091 mmol, 5 eq) was added and stirring was continued overnight. 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 2-[3-bromo-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethylamine (1.01 g, 2.796 mmol, yield=99%, purity=100%). [M+H]+=361.17

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customReaction mixture
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-fb4880f7c75d4542ad1ede73e31ddd63
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

Loading…