Ammonia → HCID 137331260, compound

HRID 2067771Notes

Reaction equation

HRID 2067771 reaction equation
Br[C:2]1[C:7]([SiH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:5]([CH3:21])=[CH:4][N:3]=1.[Br-].[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Zn+].N>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.O1CCCC1>[CH3:21][C:5]1[CH:6]=[C:7]([SiH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:2]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 131730037HCID 131730037, compoundHCID 178418723HCID 178418723, compound

Product 1

HCID 137331260HCID 137331260, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a reaction container equipped with a cooling apparatus, 2.28 g of tetrakis(triphenylphosphine)palladium, 7 g of 2-bromo-5-methyldiphenylsilylpyridine obtained in the above-mentioned Example 5-2 and 125 mL of tetrahydrofuran were added. To the obtained mixture, 39.51 mL of 2-pyridyl zinc bromide (0.5 M/tetrahydrofuran solution) was added with stirring at room temperature. The obtained mixture was stirred at 50° C. for 7 hours and 25 minutes to effect reaction. The reaction mixture was cooled until room temperature and then, 170 mL of 28% aqueous ammonia solution was added thereto. The obtained mixture was extracted three times with 200 mL of chloroform. The obtained organic layers were mixed and dried with magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated to obtain a crude product. The crude product was purified with silica gel column chromatography followed by further recrystallization with hexane to obtain 2.56 g of 5-methyldiphenylsilyl-2,2′-bipyridine.

Workup

  1. additionwere added
  2. stirringThe obtained mixture was stirred at 50° C. for 7 hours and 25 minutes
  3. customreaction
  4. temperatureThe reaction mixture was cooled until room temperature
  5. extractionThe obtained mixture was extracted three times with 200 mL of chloroform
  6. additionThe obtained organic layers were mixed
  7. dry with materialdried with magnesium sulfate
  8. customAfter removing magnesium sulfate
  9. filtrationby filtration
  10. concentrationthe filtrate was concentrated
  11. customto obtain a crude product
  12. customThe crude product was purified with silica gel column chromatography
  13. customfollowed by further recrystallization with hexane

Sources & evidence

ORD record
ord-e083f2658cd54634b431b96a03a6e2d4
Source dataset
uspto-grants-2012_10
Patent number
US08293905B2

Reaction notes

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