Triethylsilane → HCID 73060097, compound

HRID 1297280Notes

Reaction equation

HRID 1297280 reaction equation
C([SiH](CC)CC)C.C([O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]([CH:31]=[N:32][OH:33])=[C:23]2[CH3:34])=[CH:18][C:17]=1[F:35])C1C=CC=CC=1.[Cl-].[NH4+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.O1CCCC1.C(OCC)(=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2].C(OCC)(=O)C.C(N(CC)CC)C>[F:35][C:17]1[CH:18]=[C:19]([N:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]([CH:31]=[N:32][OH:33])=[C:23]2[CH3:34])[CH:20]=[CH:21][C:16]=1[OH:15]

Participants

11

Reactant 4

HCID 12052TriethylsilaneHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 86597106HCID 86597106, compound

Product 1

HCID 73060097HCID 73060097, compoundYield 56%

Reagents, catalysts & solvents 6

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 22728543Water ethylacetateSolvent

Procedure

To a stirred solution of dichloromethane (10 mL), Pd(OAc)2 (50 mg, 0.2 mmol), and triethylsilane (3 mL) was added triethylamine (1.5 mL), and the mixture was stirred at ambient temperature for 15 min. To the mixture was added 1-(4-benzyloxy-3-fluorophenyl)-2-methyl-1H-indole-3-carbaldehyde oxime (0.52 g, 1.4 mmol) in dichloromethane (15 mL), and stirring was continued for 4 hr. Ethyl acetate (25 mL) and ammonium chloride (25 mL of 10% solution) were added and the product extracted into ethyl acetate (2×25 mL). The combined organics were washed with water (3×25 mL) and brine (25 mL) and dried over MgSO4. After removing the solvent, a liquid was obtained, which was dissolved in anhydrous tetrahydrofuran (10 mL). To this stirring mixture was added tetrabutyl ammonium fluoride (3 mL). After stirring for 30 min., the mixture was taken up in ethyl acetate/water and shaken and the layers separated. The organic portion was washed with water and brine and dried over MgSO4. After evaporation of the solvent, the crude solid was purified by silica gel chromatography (25% ethyl acetate-hexanes) to give a pale yellow solid (0.22 g, 56%): mp 182-184° C.; 1H NMR (DMSO-d6): δ 2.31 (3H, s), 6.98-7.01 (1H, m), 7.07-7.17 (4H, m), 7.35 (1H, dd, J=11.7 Hz, J=2.4 Hz), 7.99-8.03 (1H, m), 8.40 (1H, s), 10.35 (1H, br s), 10.64 (1H, s); MS m/z (M+H)+ 285: Anal. for C16H13FN2O2 (0.3H2O): Calc'd: C, 66.34; H, 4.57 N, 9.30. Found: C, 66.38; H, 4.61; N, 9.85.

Workup

  1. stirringstirring
  2. waitwas continued for 4 hr
  3. extractionthe product extracted into ethyl acetate (2×25 mL)
  4. washThe combined organics were washed with water (3×25 mL) and brine (25 mL)
  5. dry with materialdried over MgSO4
  6. customAfter removing the solvent
  7. customa liquid was obtained
  8. stirringAfter stirring for 30 min.
  9. stirringshaken
  10. customthe layers separated
  11. washThe organic portion was washed with water and brine
  12. dry with materialdried over MgSO4
  13. customAfter evaporation of the solvent
  14. customthe crude solid was purified by silica gel chromatography (25% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-ecc8254c28aa41029f583ce49f9ed5ee
Source dataset
uspto-grants-2007_07
Patent number
US07250440B2

Reaction notes

Loading…