Ethyl Acetate → HCID 10853288, compound

HRID 1069630Notes

Reaction equation

HRID 1069630 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]2[C:10]([C:11]=1[CH:12](O)[C:13]([NH2:15])=[O:14])=[C:9]([O:17][CH3:18])[CH:8]=[CH:7][CH:6]=2)[CH3:2].C([SiH](CC)CC)C.C(OCC)(=O)C>FC(F)(F)C(O)=O>[CH2:1]([C:3]1[N:4]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]2[C:10]([C:11]=1[CH2:12][C:13]([NH2:15])=[O:14])=[C:9]([O:17][CH3:18])[CH:8]=[CH:7][CH:6]=2)[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 12052TriethylsilaneHCID 10735747HCID 10735747, compound

Product 1

HCID 10853288HCID 10853288, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 875 mg (2.6 mmol) of 2-ethyl-4-methoxy-alpha-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide and 0.51 mL (3.23 mmol) of triethylsilane in 10 mL of trifluoroacetic acid was stirred for 16 hours and concentrated at reduced pressure. The residue was taken up in ethyl acetate and water, the ethyl acetate separated, washed with brine and dried (MgSO4). The residue was chromatographed on silica gel and eluted first with 50% ethyl acetate/hexane and then ethyl acetate to give 521 mg (62% yield) of 2-ethyl-4-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 152-154° C.

Workup

  1. concentrationconcentrated at reduced pressure
  2. customwater, the ethyl acetate separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customThe residue was chromatographed on silica gel
  6. washeluted first with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-8820d18405274f53bad0a3a5e24aa00e
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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