Sodium Carbonate → 8-{3-[1-(4-Chloro-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-quinoline

HRID 896686Notes

Reaction equation

HRID 896686 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.CC([O-])=O.[K+].Br[C:47]1[CH:48]=[CH:49][CH:50]=[C:51]2[C:56]=1[N:55]=[CH:54][CH:53]=[CH:52]2.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.[Cl-].[NH4+].C(OCC)(=O)C.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]>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([CH:8]([C:4]2[CH:3]=[C:2]([C:47]3[CH:48]=[CH:49][CH:50]=[C:51]4[C:56]=3[N:55]=[CH:54][CH:53]=[CH:52]4)[CH:7]=[CH:6][CH:5]=2)[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:17][CH:18]=1

Participants

10

Reactant 5

HCID 10340Sodium CarbonateHCID 1401098-BromoquinolineHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 22350062HCID 22350062, compound

Product 1

HCID 101591558-{3-[1-(4-Chloro-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-quinoline

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
21 °C

Procedure

A solution of 4-[2-(3-bromo-phenyl)-2-(4-chloro-phenyl)-ethyl]-pyridine from Step 1 above (400 mg, 1.07 mmol), diboron pinacol ester (300 mg, 1.18 mmol), KOAc (315 mg, 3.2 mmol) and PdCl2(dppf) (26 mg, 0.032 mmol) in DMF (20 mL) was heated at 80° C. under N2 for 5 h. The resulting reaction mixture was cooled to 21° C., 8-bromoquinoline (290 mg, 1.4 mmol), Na2CO3 (2M, 1.61 mL, 3.2 mmol) and PdCl2(dppf) (26 mg, 0.032 mmol) was then added. The reaction mixture was stirred 18 h at 80° C., then diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 50:50 to 25:75) provided the 8-{3-[1-(4-chloro-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-quinoline compound (319 mg).

Workup

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with hexane/ethyl acetate, 50:50 to 25:75)

Sources & evidence

ORD record
ord-c4160670144347e78653a2a20994fb6e
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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