7-chlorofuro[2,3-c]pyridine-5-carboxylic acid synthesis

2synthesis methods

Product Name:7-chlorofuro[2,3-c]pyridine-5-carboxylic acid
CAS Number:478148-53-7
Molecular formula:C8H4ClNO3
Molecular Weight:197.58

Furo[2,3-c]pyridine-5-carboxaldehyde, 7-chloro-

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7-chlorofuro[2,3-c]pyridine-5-carboxylic acid

478148-53-7
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Yield:478148-53-7 55%

Reaction Conditions:

with potassium dihydrogenphosphate;NaClO₂ in water;dimethyl sulfoxide;

Steps:

1 Preparation of the Acid:

C6 (3.0 g, 16.5 mmol) is dissolved in 40 mL DMSO. KH₂PO₄ (561 mg, 4.1 mmol) in 6.5 mL water is added and then NaClO₂ (2.6 g, 23.1 mmol) in 24 mL water is added, and the reaction is stirred overnight at rt. The reaction is diluted with 200 mL water, the pH is adjusted to 9 with 2N NaOH, and any remaining aldehyde is extracted into 3*50 mL ether. The pH of the aqueous layer is adjusted to 3 with 10% aqueous HCl and is extracted with 4*50 mL EtOAc. The combined organic layer is dried over anhydrous MgSO₄, filtered, and then concentrated in vacuo to a white solid. The solid is washed with ether and is dried to afford 7-chlorofuro[2,3-c]pyridine-5-carboxylic acid (C7) (55% yield). MS (CI) for C₈H₄ClNO₃, m/z: 198 (M+H)⁺.

References:

US2003/45540,2003,A1

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Furo[3,2-c]pyridine-6-carboxamide, N-1-azabicyclo[3.2.2]non-3-yl-

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References