2-Chloroquinolin-6-ol → 4-(6-Hydroxyquinolin-2-yl)-3-(trifluoromethyl)benzoic acid

HRID 628880Notes

Reaction equation

HRID 628880 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][C:22]=2[C:31]([F:34])([F:33])[F:32])O1>>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([C:21]1[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=1[C:31]([F:32])([F:34])[F:33])[CH:11]=[CH:10]2

Participants

3

Reactant 2

HCID 221325772-Chloroquinolin-6-olHCID 66980121Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)benzoate2×

Product 1

HCID 569590634-(6-Hydroxyquinolin-2-yl)-3-(trifluoromethyl)benzoic acid

Procedure

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]+.

Sources & evidence

ORD record
ord-3cdfaeeaebfe41f7b6c6a537c0e80f78
Source dataset
uspto-grants-2016_04
Patent number
US09315462B2

Reaction notes

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