Potassium Carbonate → Ethyl (1-benzyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yloxy)acetate

HRID 1445925Notes

Reaction equation

HRID 1445925 reaction equation
[CH2:1]([N:8]1[C:12]2[N:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:11]=2[CH:10]=[C:9]1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:20][CH2:21][O:22][C:23](=[O:25])[CH3:24].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][C:16]([O:17][CH2:24][C:23]([O:22][CH2:21][CH3:20])=[O:25])=[C:11]2[CH:10]=[C:9]1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 178422233HCID 178422233, compound

Product 1

HCID 58895970Ethyl (1-benzyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yloxy)acetate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-benzyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-4-ol 7 (0.30 g, 1.26 mmol), 2-bromoethylacetate (1.05 g, 6.29 mmol) and K2CO3 (2.0 g) in anhydrous acetone (15 mL) were heated at reflux for 6 h under N2. After cooling, the mixture was filtered through celite and the filtrate was concentrated to yield a syrup. It was then re-dissolved in ethyl acetate and washed with water (10×2 mL), brine and dried (Na2SO4). The solvent was removed under reduced pressure, and the residue was chromatographed on a silica gel column eluting with 40% ethylacetate in hexanes afforded the title compound 8 as an amorphous white solid. Yield: 0.25 g, 61%; ESI MS: m/z 325.0 (M+1).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 6 h under N2
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through celite
  5. concentrationthe filtrate was concentrated
  6. customto yield a syrup
  7. washwashed with water (10×2 mL), brine
  8. dry with materialdried (Na2SO4)
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was chromatographed on a silica gel column
  11. washeluting with 40% ethylacetate in hexanes

Sources & evidence

ORD record
ord-f510f4febbda44808a9e33beafd6761e
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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