2-Chloroquinolin-6-ol → 3-Fluoro-4-(6-hydroxyquinolin-2-yl)benzoic acid

HRID 628865Notes

Reaction equation

HRID 628865 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.B([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=1[F:25])(O)O>>[F:25][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:16]=1[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)[C:20]([OH:22])=[O:21]

Participants

3

Reactant 2

HCID 221325772-Chloroquinolin-6-olHCID 231341774-(Dihydroxyboranyl)-3-fluorobenzoic acid

Product 1

HCID 569610563-Fluoro-4-(6-hydroxyquinolin-2-yl)benzoic acid

Procedure

Followed Scheme 3: Starting Materials: 2-chloroquinolin-6-ol and 4-borono-3-fluorobenzoic acid. 1H NMR (CD3OD, 400 MHz): δ 8.31 (d, J=8.4 Hz, 1H), 7.94-7.86 (m, 3H), 7.81-7.74 (m, 2H), 7.35 (dd, J=9.2, 2.8 Hz, 1H), 7.15 (d, J=2.8 Hz, 1H). MS (ESI): m/z 283.6 [M+H]+.

Sources & evidence

ORD record
ord-9cf4649676ba4454935d1e779205c445
Source dataset
uspto-grants-2016_04
Patent number
US09315462B2

Reaction notes

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