Trifluoroacetic acid → 7-(1-tert-Butylpiperidin-4-yl)-1-(2,6-dichlorophenyl)-5-(4-fluorophenyl)quinolin-2(1H)-one

HRID 394139Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]([C:12]2[CH2:13][CH2:14][N:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:16][CH:17]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:30])[N:7]2[C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29].FC(F)(F)[C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.C(O)(C(F)(F)[F:47])=O>>[C:18]([N:15]1[CH2:14][CH2:13][CH:12]([C:10]2[CH:9]=[C:8]3[C:3]([CH:4]=[CH:5][C:6](=[O:30])[N:7]3[C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])=[C:2]([C:38]3[CH:37]=[CH:36][C:35]([F:47])=[CH:34][CH:33]=3)[CH:11]=2)[CH2:17][CH2:16]1)([CH3:19])([CH3:21])[CH3:20]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 27343883-(Trifluoromethyl)phenylboronic acid

HCID 226481935-Bromo-7-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(2,6-dichlorophenyl)quinolin-2(1h)-one

Product 1

HCID 226481277-(1-tert-Butylpiperidin-4-yl)-1-(2,6-dichlorophenyl)-5-(4-fluorophenyl)quinolin-2(1H)-one

Procedure

The title compound was prepared from 5-bromo-7-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(2,6-dichlorophenyl)quinolin-2(1H)-one (INTERMEDIATE ABA5) and using 3-trifluoromethylphenylboronic acid as described in EXAMPLE ABA11. 1H NMR (CD3OD, 500 MHz) TFA salt: δ 1.358 (s, 9H), 1.780 (q, J=10.5, 12.8 Hz, 2H), 2.062 (d, J=15.6 Hz, 2H), 2.702 (m, 1H), 3.004 (t, J=13.0 Hz, 2H), 3.612 (d, J=13.0 Hz, 2H), 6.460 (s, 1H), 6.682 (d, J=10.2 Hz, 1H), 7.204 (s, 1H), 7.565 (t, J=8.8 Hz, 1H) 7.672-7.742 (m, 5H), 7.778 (m, 1H), 7.844 (d, J=10.2 Hz, 1H). Mass spectrum (ESI): 573.5 (M+1).

Sources & evidence

ORD record: ord-40e4b3067d8845c0844538a816fc3a8a
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809199B2

Reaction notes

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