Chlorotrimethylsilane → HCID 67287344, compound

HRID 1626445Notes

Reaction equation

HRID 1626445 reaction equation
[BH4-].[Li+].Cl[Si](C)(C)C.[CH3:8][O:9][C:10]1[C:15]([CH:16]=[CH:17][N+:18]([O-])=O)=[CH:14][CH:13]=[C:12]([C:21]([F:24])([F:23])[F:22])[N:11]=1>O1CCCC1>[CH3:8][O:9][C:10]1[C:15]([CH2:16][CH2:17][NH2:18])=[CH:14][CH:13]=[C:12]([C:21]([F:24])([F:23])[F:22])[N:11]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 67288650HCID 67288650, compound

Product 1

HCID 67287344HCID 67287344, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium borohydride (71.2 mg, 3.27 mmol) in tetrahydrofuran (5 ml) was added chlorotrimethylsilane (826 μl, 6.53 mmol) at ambient temperature (exothermic reaction) and the reaction was allowed to stir for 30 minutes. 2-Methoxy-3-(2-nitrovinyl)-6-(trifluoromethyl)pyridine (193 mg, 0.778 mmol) was added, and the reaction was heated to reflux for 6 hours. The reaction was cooled to ambient temperature and quenched by the addition of 1M HCl (9 ml). After 15 minutes, the reaction was diluted with water and washed with ether and hexanes. The aqueous layer was adjust to pH 13 with 5 N aqueous sodium hydroxide and extracted with ethyl acetate (2×25 ml). The combined ethyl acetate extractions were dried over Na2SO4, filtered, and concentrated to yield the desired compound (143 mg, 0.649 mmol, 83.5% yield).

Workup

  1. custom(exothermic reaction)
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 6 hours
  4. customquenched by the addition of 1M HCl (9 ml)
  5. waitAfter 15 minutes
  6. additionthe reaction was diluted with water
  7. washwashed with ether and hexanes
  8. extractionextracted with ethyl acetate (2×25 ml)
  9. extractionThe combined ethyl acetate extractions
  10. dry with materialwere dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-9443c74c515d488e8798f9c657b331ab
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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