Cesium carbonate → HCID 66915552, compound

HRID 1850034Notes

Reaction equation

HRID 1850034 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[F:9].[N:10]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[C:14]=2[CH:13]=[CH:12][CH:11]=1.C([O-])(=O)C.[K+].C([O-])([O-])=O.[Cs+].[Cs+]>CS(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]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:14]=2[CH:13]=[CH:12][CH:11]=[N:10]3)=[CH:4][C:3]=1[F:9]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 517044Potassium AcetateHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 5153389Quinolin-5-ylboronic acid

Product 1

HCID 66915552HCID 66915552, compoundYield 104%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

4-Bromo-3-fluoroiodobenzene (250 mg, 0.8 mmol, 1.2 eq.), quinoline-5-boronic acid (120 mg, 0.7 mmol), potassium acetate (70 mg, 1 eq.), Pd(dppf)Cl2 (70 mg, 0.1 eq.), and Cs2CO3 (700 mg, 3.0 eq.) in DMSO (5 mL) were heated under argon at 80° C. during 1 h. The reaction mixture was extracted from water into ether, dried over Na2SO4, concentrated, and chromatographed on silica gel (5→20% EtOAc/hexanes) to give 5-(4-bromo-3-fluorophenyl)quinoline (220 mg, quant.).

Workup

  1. extractionThe reaction mixture was extracted from water into ether
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customchromatographed on silica gel (5→20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-77243fe0a7cc496d92b0f006515e02b7
Source dataset
uspto-grants-2015_02
Patent number
US08957049B2

Reaction notes

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