4-(4-Chloro-3-fluoro-6-methoxyquinolin-2-yl)benzoic acid → 4-(3-Fluoro-6-methoxyquinolin-2-yl)benzoic acid

HRID 1472652Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)[C:3]=1[F:23]>CO.[Pd]>[F:23][C:3]1[C:4]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)=[N:5][C:6]2[C:11]([CH:2]=1)=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of the mixture from Step 1 in absolute MeOH (5 mL) was added Pd/C (10% Pd, 100 mg). The mixture was stirred at 25° C. for 1 hour under H2 atmosphere. The solids were filtered off and the filtrate was concentrated to give the product (60 mg, two-step yield 66%).

Workup

filtrationThe solids were filtered off
concentrationthe filtrate was concentrated
customto give the product (60 mg, two-step yield 66%)

Sources & evidence

ORD record: ord-482bca3b3cbb49699fb69bd8b6c69de1
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012646B2

Reaction notes

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