Ethyl Acetate → (1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetic acid

HRID 2169428Notes

Reaction equation

HRID 2169428 reaction equation
[N+](=CC([C:6]1([N:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[CH:13]=[CH:12]2)[CH2:10][CH2:9][CH2:8][CH2:7]1)=O)=[N-].[C:20]([O:23]CC)(=[O:22])[CH3:21]>O1CCOCC1.O.CCCCCC>[N:11]1([C:6]2([CH2:21][C:20]([OH:23])=[O:22])[CH2:10][CH2:9][CH2:8][CH2:7]2)[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH:13]=[CH:12]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 867260572-Diazo-1-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-ethanone

Product 1

HCID 86726059(1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetic acidYield 54%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a stirred solution of 2-diazo-1-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-ethanone (396) (0.95 g, 3.82 mmol) in dioxane:water (10:1) (27.5 mL) was added silveracetate (319 mg, 1.91 mmol) and stirring was continued for 2 h at room temperature (TLC, 30% ethyl acetate in hexane, Rf=0.2). The mixture was filtered over a celite bed, washed with ethyl acetate (3×20 mL) and concentrated. The crude product was purified by Combi-Flash column (eluted at 30% ethyl acetate in hexane) to get (1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetic acid (397) (0.5 g, 54%) as a brown solid.

Workup

  1. filtrationThe mixture was filtered over a celite bed
  2. washwashed with ethyl acetate (3×20 mL)
  3. concentrationconcentrated
  4. customThe crude product was purified by Combi-Flash column (eluted at 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e9f328272010419887503c6f2df30005
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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