Sodium Carbonate → HCID 57808558, compound

HRID 2105527Notes

Reaction equation

HRID 2105527 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C([O-])(=O)C.[K+].Br[C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[N:6]=[CH:7][C:2]([C:27]3[N:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[CH:3][C:4]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 517044Potassium AcetateHCID 59771326HCID 59771326, compound

Product 1

HCID 57808558HCID 57808558, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5-Chloro-2-(4-methylphenyl)-3-phenylpyridine (10-2; 0.050 g, 0.179 mmol), bis(pinacoloto)diboron (0.054 g, 0.214 mmol), potassium acetate (0.026 g, 0.268 mmol), Pd2(dba)3 (5 mg, 0.005 mmol) tricyclohexylphosphine (4 mg, 0.013 mmol) in anhydrous dioxane (2 mL) was degassed (3× pump/N2) and heated at 160° C. in the microwave for 1 hr. forms the boronic acid. In the same pot, 2-bromopyrimidine (0.042 g, 0.26mmol), tetrakis(triphenylphosphine)palladium (0.010 g, 0.00895 mmol), and 2M aq Na2CO3 (1 mL) were added and the resulting mixture was degassed (3× pump/N2) and heated in the microwave at 150° C. for 3 hr. Reaction partitioned between CH2Cl2 and water, extracted 3× with CH2Cl2, and the combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography (10-20% EtOAc in Hexanes) to give the title compound. 1H-NMR (500 MHz, CDCl3) δ 9.69 (d, 1H, J=2.0 Hz), 8.86 (d, 2H, J=4.9 Hz), 8.73 (d, 1H, J=2.0 Hz), 7.37-7.23 (m, 8H), 7.08 (d, 2H J=7.82 Hz), 2.33 (s, 3H). LRMS m/z (M+H) Calcd: 324.0, found: 324.0.

Workup

  1. customwas degassed (3× pump/N2)
  2. customthe resulting mixture was degassed (3× pump/N2)
  3. temperatureheated in the microwave at 150° C. for 3 hr
  4. customReaction
  5. custompartitioned between CH2Cl2 and water
  6. extractionextracted 3× with CH2Cl2
  7. dry with materialthe combined organics were dried (anhd. Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel chromatography (10-20% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-e2b479cc043847138ac11a29bf621133
Source dataset
uspto-grants-2009_08
Patent number
US07579355B2

Reaction notes

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