Sodium Carbonate → 5'-Bromo-2'-chloro-2-methyl-[3,4']bipyridinyl

HRID 347686Notes

Reaction equation

HRID 347686 reaction equation
[CH3:1][C:2]1[C:7](OS(C(F)(F)F)(=O)=O)=[CH:6][CH:5]=[CH:4][N:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].[Br:39][C:40]1[C:41](I)=[CH:42][C:43]([Cl:46])=[N:44][CH:45]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[Br:39][C:40]1[C:41]([C:7]2[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:42][C:43]([Cl:46])=[N:44][CH:45]=1

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 107764652-Methylpyridin-3-yl trifluoromethanesulfonateHCID 218651405-Bromo-2-chloro-4-iodopyridine

Product 1

HCID 210836365'-Bromo-2'-chloro-2-methyl-[3,4']bipyridinyl

Reagents, catalysts & solvents 3

HCID 53485975CID 53485975Catalyst2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2.73 g (11.3 mmol) trifluoro-methanesulfonic acid 2-methyl-pyridin-3-yl ester, 3.16 g (12.4 mmol) bis(pinacolato)diboron, 3.33 g (33.9 mmol) potassium acetate and 0.46 g (0.56 mmol) dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct in 75 ml N,N-dimethylformamide was heated at 80° C. over night under argon. After cooling to room temperature 5.40 g (17.0 mmol) 5-bromo-2-chloro-4-iodo-pyridine, another portion of 0.46 g (0.56 mmol) dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct and 30 ml of a deoxygenated 2 M aqueous solution of sodium carbonate were added. The reaction mixture was heated at 80° C. for 4.5 h. After cooling to room temperature the mixture was diluted with water and extracted with three portions of tert-butyl methyl ether. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 1.00 (31%) of the title compound as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was heated at 80° C. for 4.5 h
  2. temperatureAfter cooling to room temperature the mixture
  3. extractionextracted with three portions of tert-butyl methyl ether
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f81d9b9275dd4c88bebb38278d438da4
Source dataset
uspto-grants-2007_02
Patent number
US07176205B2

Reaction notes

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