Monobasic potassium phosphate → 3-Bromofuro[2,3-c]pyridine-5-carboxylic acid

HRID 1830556Notes

Reaction equation

HRID 1830556 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH:11]=[O:12])[CH:9]=2)[O:4][CH:3]=1.[OH:13]P([O-])(O)=O.[K+]>C1COCC1.CC(O)(C)C.O>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[O:4][CH:3]=1

Participants

6

Reactant 2

HCID 516951Monobasic potassium phosphateHCID 22047043HCID 22047043, compound

Product 1

HCID 220476273-Bromofuro[2,3-c]pyridine-5-carboxylic acidYield 100.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Bromofuro[2,3-c]pyridine-5-carbaldehyde (3.26 g, 14.42 mmol) is dissolved in THF (100 mL)/t-BuOH (50 mL)/H2O (50 mL), treated with a single portion of NaOCl2 (4.89 g, 43.3 mmol) and KH2PO4 (3.92 g, 28.8 mmol) and stirred at rt for 18 h. The white solid is collected via filtration and the filtrate is concentrated in vacuo to dryness. The residue is suspended in water (25 mL), acidified to pH 2 with concentrated HCl and the resulting solid collected via filtration. The collected solids are dried in a vacuum oven at 50° C. for 18 h and combined to afford 3.52 g (99%) of 3-bromofuro[2,3-c]pyridine-5-carboxylic acid as a white solid. MS (EI) m/z: 241 (M+).

Workup

  1. filtrationThe white solid is collected via filtration
  2. concentrationthe filtrate is concentrated in vacuo to dryness
  3. filtrationthe resulting solid collected via filtration
  4. customThe collected solids are dried in a vacuum oven at 50° C. for 18 h

Sources & evidence

ORD record
ord-4fb05a223d544594af743f48ec0abb42
Source dataset
uspto-grants-2006_06
Patent number
US07067515B2

Reaction notes

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