Acetonitrile → HCID 58524335, compound

HRID 1678781Notes

Reaction equation

HRID 1678781 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6]([C:12]1[CH:19]=[CH:18][C:15](C=O)=[CH:14][CH:13]=1)=[N:7]2.[C:26](NC(=O)[O-])([CH3:29])([CH3:28])[CH3:27].C([SiH](CC)CC)C.FC(F)(F)[C:43]([OH:45])=[O:44].C([O-])(O)=O.[Na+].[C:53](#[N:55])C>>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:6]([C:12]1[CH:13]=[CH:14][C:15]([CH2:53][NH:55][C:43](=[O:44])[O:45][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:18][CH:19]=1)=[N:7]2

Participants

7

Reactant 6

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 21252905Tert-butylcarbamateHCID 575007324-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde

Product 1

HCID 58524335HCID 58524335, compound

Procedure

To a stirred solution of 9-1 (7 g, 20.2 mMol) and t-butylcarbamate (2.6 g, 22.3 mMol) in dry acetonitrile (35 mL) was added triethylsilane (29.1 mL, 182 mMol) followed by trifluoroacetic acid (6 mL, 81 mMol). After stirring for 3 hours, the solution was poured into aqueous NaHCO3 and was extracted into ethyl acetate three times. The combined organic layers were washed with water followed by brine. The organic layer was then dried with Na2SO4, filtered, and concentrated in vacuo and purified using flash chromatography on silica. LC/MS (M+1) calculated: 446.9; observed: 446.1

Workup

  1. extractionwas extracted into ethyl acetate three times
  2. washThe combined organic layers were washed with water
  3. dry with materialThe organic layer was then dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified

Sources & evidence

ORD record
ord-a2a7d347789048a9888585f3932b2e1e
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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