4-chloro-1-(4-methoxybenzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethyl ester → Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1470281Notes

Reaction equation

HRID 1470281 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([Cl:24])=[C:8]2[CH:14]=[CH:13][N:12](CC3C=CC(OC)=CC=3)[C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]>C(O)(C(F)(F)F)=O.OS(O)(=O)=O.C1(OC)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([Cl:24])=[C:8]2[CH:14]=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 578991914-chloro-1-(4-methoxybenzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 53438275Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylateYield 46.3%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidSolventHCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

To a solution of 4-chloro-1-(4-methoxybenzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethyl ester (prepared as described in J. Heterocycl. Chem. 1972, 235 and Bioorg. Med. Chem. Lett. 2003, 2405) (3.48 g, 10 mmol) in TFA (20 mL), conc. H2SO4 (1.5 mL) and anisole (3 mL) were added at room temperature. The resulting solution was stirred at this temperature for 3 hours and then basified slowly by addition of ice-cold aqueous NaHCO3. The aqueous solution was extracted with ethyl acetate and the combined organic layers were dried (Na2SO4) and concentrated. The residue was filtered and washed with n-hexanes to give a yellow solid (1.04 g, 46%). LC-MS (LCT2) m/z 226 [M+H±], Rt 6.22 min.

Workup

  1. additionbasified slowly by addition of ice-cold aqueous NaHCO3
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. filtrationThe residue was filtered
  6. washwashed with n-hexanes

Sources & evidence

ORD record
ord-9ebc07c203bf48b8be0758fa3d85187d
Source dataset
uspto-grants-2015_04
Patent number
US09006430B2

Reaction notes

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