3-Bromopyridine → HCID 178420147, compound

HRID 2096353Notes

Reaction equation

HRID 2096353 reaction equation
CC(C)([O-])C.[Na+].Br[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[C:14]1([C:20]2[N:25]=[CH:24][C:23]([C:26]3[N:27]=[C:28]([CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)[NH:29][CH:30]=3)=[CH:22][N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(C)(C)C.C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]1([C:20]2[N:25]=[CH:24][C:23]([C:26]3[N:27]=[C:28]([CH:31]4[CH2:36][CH2:35][N:34]([C:8]5[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=5)[CH2:33][CH2:32]4)[NH:29][CH:30]=3)=[CH:22][N:21]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 3

HCID 122863-BromopyridineHCID 23676156Sodium t-butoxideHCID 178420149HCID 178420149, compound

Product 1

HCID 178420147HCID 178420147, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

The title compound is prepared in a similar manner as described in Tetrahedron Letters, 2007, 48(14), 2519-2525. In this case, to a degassed solution of sodium tert-butoxide, palladium acetate, and 2-dicyclohexlphosphino-2′,4′,6′-triisopropylbiphenyl (X-phos) in tert-butanol and toluene is added 3-bromopyridine and 2-phenyl-5-(2-(piperidin-4-yl)-1H-imidazol-4-yl)pyrimidine. The reaction is stirred and heated at 120° C. under nitrogen for 18 hours. The reaction mixture is cooled, diluted with water and the organic material is extracted with ethyl acetate. The organic phase is washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is chromatographed on silica to give the title compound.

Workup

  1. customThe title compound is prepared in a similar manner
  2. temperatureThe reaction mixture is cooled
  3. extractionthe organic material is extracted with ethyl acetate
  4. washThe organic phase is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-7e2839f7579f48f6ae9c1925e442fd88
Source dataset
uspto-grants-2013_05
Patent number
US08450326B2

Reaction notes

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