Sodium Carbonate → 4-(7-Methoxyquinolin-3-yl)benzoic acid

HRID 2201476Notes

Reaction equation

HRID 2201476 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.B([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:13][O:12][C:7]1[CH:6]=[C:5]2[C:10]([CH:11]=[C:2]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)[CH:3]=[N:4]2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 187885483-Bromo-7-methoxyquinoline2×

Product 1

HCID 679746684-(7-Methoxyquinolin-3-yl)benzoic acidYield 29.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 3-bromo-7-methoxyquinoline (Intermediate 13, 380 mg, 1.6 mmol), 4-boronobenzoic acid (266 mg, 1.6 mmol) and Na2CO3 (848 mg, 8.0 mmol) in DME/H2O/EtOH (5 mL, V/V/V=1/1/0.5) was added Pd(dppf)Cl2 (585 mg, 0.8 mmol). The mixture was heated to 120° C. by microwave for 1 h. The mixture was partitioned between water (20 mL) and ethyl acetate (20 mL). The aqueous phase was separated and acidified to pH=3 with 1 N HCl. The precipitate was filtered and dried in vacuo to afford product as a powder (130 mg, 29.1%).

Workup

  1. customThe mixture was partitioned between water (20 mL) and ethyl acetate (20 mL)
  2. customThe aqueous phase was separated
  3. filtrationThe precipitate was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-67fd4dcd159f4804a728d828894ba1db
Source dataset
uspto-grants-2016_06
Patent number
US09364481B2

Reaction notes

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