Dichloromethane → HCID 58154813, compound

HRID 2359432Notes

Reaction equation

HRID 2359432 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:12]([O-:14])=[O:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[F:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[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]>[F:15][C:16]1[CH:17]=[C:18]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([N+:12]([O-:14])=[O:13])[CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 3194532-Chloro-8-nitroquinolineHCID 27831923-Fluoro-5-(trifluoromethyl)benzeneboronic acid

Product 1

HCID 58154813HCID 58154813, compound

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-chloro-8-nitroquinoline (0.580 g, 2.78 mmol), 3-fluoro-5-(trifluoromethyl)phenylboronic acid (0.675 g, 3.22 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 sodium bicarbonate solution and the mixture was extracted with ethyl acetate (3×20 mL). The organic layers were combined, washed with brine, dried (MgSO4), and concentrated to yield 2-(3-fluoro-5-(trifluoromethyl)phenyl)-8-nitroquinoline. The product was used without further purification.

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

Sources & evidence

ORD record
ord-a31c5d325bfe427f91fe138225860dca
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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