Triethylamine → Trifluoromethanesulfonic acid 7-trifluoromethoxyisoquinolin-3-yl ester

HRID 1926263Notes

Reaction equation

HRID 1926263 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9](F)=[C:8]2[C:3]=1[CH:4]=[C:5]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])[N:6]=[CH:7]2.[F:21][C:22]([F:36])([F:35])[O:23]C1C=C2C(C=C(O)N=C2)=CC=1.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.CCN(CC)CC>C(Cl)Cl>[F:21][C:22]([F:36])([F:35])[O:23][C:10]1[CH:9]=[C:8]2[C:3]([CH:4]=[C:5]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])[N:6]=[CH:7]2)=[CH:2][CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86633140Trifluoromethanesulfonic acid 5-chloro-8-fluoroisoquinolin-3-yl esterHCID 178515360HCID 178515360, compound

Product 1

HCID 86633143Trifluoromethanesulfonic acid 7-trifluoromethoxyisoquinolin-3-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By following the procedure for the preparation of trifluoromethanesulfonic acid 5-chloro-8-fluoroisoquinolin-3-yl ester, the title compound was prepared from 7-trifluoromethoxyisoquinolin-3-ol (0.98 g, 4.3 mmol), triflic anhydride (0.17 mL, 1.0 mmol), NEt3 (0.8 mL, 3.0 mmol) and CH2Cl2 (10 mL). 1H NMR (CDCl3, 300 MHz): δ=7.63 (s, 1H), 7.65 (d, J=6.0 Hz, 1H), 7.89 (s, 1H), 7.98 (d, J=9.0 Hz, 1H), 9.10 (s, 1H).

Sources & evidence

ORD record
ord-e997272bd81b42438d23977ca11733ec
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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