Acetic Acid → 5-Methoxy-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acid

HRID 751630Notes

Reaction equation

C([O:3][C:4]([C:6]1[NH:14][C:13]2[C:8](=[N:9][C:10]([O:15][CH3:16])=[CH:11][CH:12]=2)[CH:7]=1)=[O:5])C.[OH-].[Na+].C(O)(=O)C>C(O)C>[CH3:16][O:15][C:10]1[N:9]=[C:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[NH:14][C:13]2=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 5-methoxy-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester (Preparation 35, 128 mg, 0.58 mmol) in ethanol (10 mL, absolute) was added aqueous sodium hydroxide (0.35 mL, 2M) and the mixture heated to 70° C. for 3 h then cooled to rt. The solution was adjusted to pH 4 by addition of glacial acetic acid and the solvents removed under reduced pressure. Ethyl acetate (20 mL) was added to the resulting oil and the mixture sonicated until a fine suspension formed. The mother liquor was decanted and the remaining solid was washed with ethyl acetate and dried in vacuo to give the title compound as a pale orange powder. δH (CD3OD): 3.92 (3H, s), 6.63 (1H, d), 6.94 (1H, s), 7.72 (1H, d).

Workup

temperaturethen cooled to rt
customthe solvents removed under reduced pressure
additionEthyl acetate (20 mL) was added to the resulting oil
customthe mixture sonicated until a fine suspension
customformed
customThe mother liquor was decanted
washthe remaining solid was washed with ethyl acetate
customdried in vacuo

Sources & evidence

ORD record: ord-c0bdaa67aaa343f8b1337f2513b19664
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405210B2

Reaction notes

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