Triethylsilane → 4-{3-[(Hydroxyimino)methyl]-2-methyl-1H-indol-1-yl}phenol

HRID 1297277Notes

Reaction equation

HRID 1297277 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][CH:17]=1)C1C=CC=CC=1.[Cl-].[NH4+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.O1CCCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C(OCC)(=O)C.C(N(CC)CC)C>[OH: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][CH:17]=1

Participants

10

Reactant 4

HCID 12052TriethylsilaneHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 86597104HCID 86597104, compound

Product 1

HCID 714069174-{3-[(Hydroxyimino)methyl]-2-methyl-1H-indol-1-yl}phenolYield 83%

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of dichloromethane (20 mL), Pd(OAc)2 (50 mg, 0.2 mmol), and triethylsilane (2 mL) was added triethylamine (1 mL), and the mixture was stirred at room temperature for 15 min. To the mixture was added 1-(4-benzyloxyphenyl)-2-methyl-1H-indole-3-carbaldehyde oxime (0.36 g, 1 mmol) in dichloromethane (10 mL), and stirred for 90 min. 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 organic layers 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 mixture was added tetrabutyl ammonium fluoride (3 mL). After stirring for 30 min, the mixture was extracted with ethyl acetate and water. The organic layer was washed with water and brine and dried over MgSO4. After evaporation of the solvent afforded the crude solid which was purified by silica gel chromatography (25% ethyl acetate-hexanes) to give a pale yellow solid (83%): mp 171-173° C.; 1H NMR (DMSO-d6): δ 2.29 (3H, s), 6.95 (4H, d, J=7.7 Hz), 7.09-7.13 (2H, m), 7.22 (2H, d, J=8.7 Hz), 7.98-8.01 (1 H, m), 8.40 (1H, s), 9.89 (1H, s), 10.63 (1H, s); MS m/z (M+H)+ 267. Anal. for C16H14N2O2: Calc'd: C, 72.17; H, 5.30; N, 10.52. Found: C, 71.78; H, 5.23; N, 10.37.

Workup

  1. stirringstirred for 90 min
  2. extractionthe product extracted into ethyl acetate (2×25 mL)
  3. washThe combined organic layers were washed with water (3×25 mL) and brine (25 mL)
  4. dry with materialdried over MgSO4
  5. customAfter removing the solvent
  6. customa liquid was obtained
  7. stirringAfter stirring for 30 min
  8. extractionthe mixture was extracted with ethyl acetate and water
  9. washThe organic layer was washed with water and brine
  10. dry with materialdried over MgSO4
  11. customAfter evaporation of the solvent
  12. customafforded the crude solid which
  13. customwas purified by silica gel chromatography (25% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-2e5d2aeb08cb4249aa8352d777702864
Source dataset
uspto-grants-2007_07
Patent number
US07250440B2

Reaction notes

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