Monobasic potassium phosphate → 7-Iodofuro[3,2-c]pyridine-2-carboxylic acid

HRID 217177Notes

Reaction equation

HRID 217177 reaction equation
OP([O-])(O)=O.[K+].[I:7][C:8]1[C:9]2[O:16][C:15]([CH:17]=[O:18])=[CH:14][C:10]=2[CH:11]=[N:12][CH:13]=1.[O-:19]Cl=O.[Na+]>O.CS(C)=O>[I:7][C:8]1[C:9]2[O:16][C:15]([C:17]([OH:19])=[O:18])=[CH:14][C:10]=2[CH:11]=[N:12][CH:13]=1

Participants

6

Reactant 3

HCID 516951Monobasic potassium phosphate2×HCID 23668197Sodium Chlorite2×HCID 591087597-Iodofuro[3,2-c]pyridine-2-carbaldehyde

Product 1

HCID 576594527-Iodofuro[3,2-c]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent4×

Procedure

A solution of KH2PO4 (81 mg, 0.59 mmol) in H2O (3 mL) was added to a solution of 7-iodofuro[3,2-c]pyridine-2-carbaldehyde (578 mg, 2.12 mmol) in DMSO (16 mL). The stirred mixture was treated carefully with a solution of NaClO2 (335 mg, 2.96 mmol) in H2O (5 mL). After 16 h, more KH2PO4 (81 mg, 0.59 mmol) in H2O (3 mL) and NaClO2 (335 mg, 2.96 mmol) in H2O (5 mL) were added, then stirring was continued for a further 48 h. The precipitated solid was collected, washed with DMSO, H2O, i-PrOH, and EtOAc, and vacuum-dried to furnish the title compound: m/z (ES+)=289.9 [M+H]+.

Workup

  1. waitwas continued for a further 48 h
  2. customThe precipitated solid was collected
  3. washwashed with DMSO, H2O, i-PrOH, and EtOAc
  4. customvacuum-dried

Sources & evidence

ORD record
ord-83b66e76e2d844a58e71bd9fb500c207
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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