Réaction #84084

ord-e19cf6defb5943c1ab8067e45c261391

Équation de réaction

Oc1ccc2nc(Cl)ccc2c1
2-chloroquinolin-6-ol
COC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)c(C(F)(F)F)c1
methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)benzoate
COC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)c(C(F)(F)F)c1
Intermediate 5
COC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)c(C(F)(F)F)c1
methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)benzoate
O=C(O)c1ccc(-c2ccc3cc(O)ccc3n2)c(C(F)(F)F)c1
4-(6-hydroxyquinolin-2-yl)-3-(trifluoromethyl)benzoic acid

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

Followed Scheme 3: starting with 2-chloroquinolin-6-ol and methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)benzoate (Intermediate 5). 1H NMR (DMSO-d6, 400 MHz): δ 10.21 (brs, 1H), 8.35-8.25 (m, 3H), 7.89 (d, J=9.2 Hz, 1H), 7.79 (d, J=8.0 Hz, 1H), 7.57 (d, J=8.4 Hz, 1H), 7.38 (dd, J=9.2, 2.8 Hz, 1H), 7.23 (d, J=2.4 Hz, 1H). MS (ESI): m/z 333.7 [M+H]+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09433618B2uspto-grants-2016_09