Dichloromethane → 2-(5-Methylpyridin-3-yl)quinoline-8-carboxylic acid

HRID 2359435Notes

Reaction equation

HRID 2359435 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[N:20][CH:21]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>CN(C=O)C.O.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]>[CH3:15][C:16]1[CH:17]=[C:18]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:19]=[N:20][CH:21]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27627085-Methylpyridine-3-boronic acidHCID 190262012-Chloroquinoline-8-carboxylic acid

Product 1

HCID 581546112-(5-Methylpyridin-3-yl)quinoline-8-carboxylic acidYield 72.1%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 2-chloroquinoline-8-carboxylic acid (0.600 g, 2.8 mmol), 5-methylpyridin-3-ylboronic acid (0.410 g, 3.0 mmol), K3PO4 (1.1 g, 5.2 mmol), and Pd(dppf)Cl2.CH2Cl2 (0.10 g, 0.122 mmol) in DMF (3 mL) and water (1 mL) was microwave heated (125° C.×1 Hour). The mixture was filtered over celite and the celite cake was washed with ethyl acetate (30 mL). The filtrate was combined with 60 mL aqueous saturated NaHCO3 solution and the mixture was extracted with ethyl acetate (3×20 mL). The organic layers were combined, washed with brine, dried (MgSO4), and concentrated. The crude material was purified by flash chromatography (a gradient of 0 to 100% ethyl acetate in pentane) to obtain 2-(5-methylpyridin-3-yl)quinoline-8-carboxylic acid (0.535 g, 2.02 mmol).

Workup

  1. filtrationThe mixture was filtered over celite
  2. washthe celite cake was washed with ethyl acetate (30 mL)
  3. extractionthe mixture was extracted with ethyl acetate (3×20 mL)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography (a gradient of 0 to 100% ethyl acetate in pentane)

Sources & evidence

ORD record
ord-f9bb6a143c27405c83db57eab064cfba
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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