Chlorotrimethylsilane → HCID 15379438, compound

HRID 53171Notes

Reaction equation

HRID 53171 reaction equation
BrCCBr.C[Si](Cl)(C)C.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Br[C:19]1[CH:20]=[C:21]2[O:27][C:26](=[O:28])[N:25]([CH3:29])[C:22]2=[N:23][CH:24]=1>O1CCCC1.[Zn].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>[CH3:29][N:25]1[C:22]2=[N:23][CH:24]=[C:19]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:20]=[C:21]2[O:27][C:26]1=[O:28]

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7498Benzyl BromideHCID 78391,2-DibromoethaneHCID 159260166-Bromo-3-methyl[1,3]oxazolo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 15379438HCID 15379438, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Zinc (227 mg, 3.48 mmol) is suspended in tetrahydrofuran (10 ml) and 1,2-dibromoethane (0.22 ml, 0.2 mmol) is added. The mixture is heated at 60° C. for 3 minutes, the solution is allowed to cool until the temperature is 35° C., and trimethylsilyl chloride (0.06 ml, 0.5 mmol) is slowly added. Stirring is maintained for 30 minutes and then benzyl bromide (0.11 ml, 0.9 mmol) is added. Wait a further 30 minutes before introducing 6-bromo-3-methyloxazolo[4,5-b]pyridin-2(3H)-one (200 mg, 0.87 mmol) and tetrakis(triphenylphosphine)palladium (4 mg). Heat at 50° C. for 20 minutes. After the solution has been cooled, the zinc is removed by filtration, the flitrate is taken up in water, and then a 10% aqueous hydrochloric acid solution is added until the aqueous phase becomes clear. Extraction is carried out with dichloromethane. The organic phase is dried over magnesium sulfate and filtered, and then the solvent is evaporated off under reduced pressure. The title product is purified by chromatography on silica gel (eluant: dichloromethane). The yield obtained is 91%. ##STR51##

Workup

  1. temperatureto cool until the temperature
  2. customis 35° C.
  3. temperatureis maintained for 30 minutes
  4. temperatureHeat at 50° C. for 20 minutes
  5. temperatureAfter the solution has been cooled
  6. customthe zinc is removed by filtration
  7. additiona 10% aqueous hydrochloric acid solution is added until the aqueous phase
  8. extractionExtraction
  9. dry with materialThe organic phase is dried over magnesium sulfate
  10. filtrationfiltered
  11. customthe solvent is evaporated off under reduced pressure
  12. customThe title product is purified by chromatography on silica gel (eluant: dichloromethane)
  13. customThe yield obtained

Sources & evidence

ORD record
ord-b4a73ef744a14bab9fa46296894a21b5
Source dataset
uspto-grants-1997_04
Patent number
US05618819

Reaction notes

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