Reaction #84093

Reaction equation

2-chloro-4-fluoro-6-methoxyquinoline

Intermediate 7

2-chloro-4-fluoro-6-methoxyquinoline

4-carboxy-2-fluorophenylboronic acid

→

desired product

3-fluoro-4-(4-fluoro-6-hydroxyquinolin-2-yl)benzoic acid

Conditions

Workup

1. 1
   OtherThe compound was prepared
2. 2
   OtherIn step 2, after purification by prep HPLC
3. 3
   ExtractionNaHCO3 to pH 6, followed by extraction with EtOAc/MeOH (v/v=10/1, 50 mL×3)
4. 4
   WashCombined organics were washed with brine (50 mL)
5. 5
   Dryingdried over Na2SO4
6. 6
   Concentrationconcentrated in vacuo

Procedure

The compound was prepared following Scheme 2, B conditions starting from 2-chloro-4-fluoro-6-methoxyquinoline (Intermediate 7) and 4-carboxy-2-fluorophenylboronic acid. Note: In step 2, after purification by prep HPLC, the collected fractions were immediately neutralized with sat.NaHCO3 to pH 6, followed by extraction with EtOAc/MeOH (v/v=10/1, 50 mL×3). Combined organics were washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuo to give the desired product. 1H NMR (MeOD 400 MHz): δ 8.10-8.00 (m, 2H), 7.98 (dd, J=8.0, 1.2 Hz, 1H), 7.85 (dd, J=11.6, 1.2 Hz, 1H), 7.62 (dd, J=11.6, 2.0 Hz, 1H), 7.45 (dd, J=9.2, 2.8 Hz, 1H), 7.31 (d, J=2.8 Hz, 1H). MS (ESI): m/z 301.8 [M+H]+.

Source