Water → 2-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid

HRID 564726Notes

Reaction equation

HRID 564726 reaction equation
Br[C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]2[O:10][C:11]([C:13]([O:17][CH3:18])([O:15][CH3:16])[CH3:14])=[CH:12][C:3]=12.C1(P(C(P(C2C=CC=CC=2)C2C=CC=CC=2)(C)C)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[O:55]1[CH2:59]CCC1.[OH2:60]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:16][O:15][C:13]([C:11]1[O:10][C:4]2[C:5]([O:8][CH3:9])=[N:6][CH:7]=[C:2]([C:59]([OH:55])=[O:60])[C:3]=2[CH:12]=1)([O:17][CH3:18])[CH3:14]

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12091099Phosphine, (1-methylethylidene)bis[diphenyl-HCID 221128034-Bromo-2-(1,1-dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine

Product 1

HCID 221128202-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acidYield 30%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
90 °C

Procedure

4-Bromo-2-(1,1-dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine (1.0 g), palladium acetate (71 mg), bis-diphenylphosphinopropane (0.26 g), triethylamine (4.4 ml), tetrahydrofuran (60 ml) and water (30 ml) were combined in a Parr pressure reactor. The vessel was purged with carbon monoxide 3 times before being charged with carbon monoxide at 965 kPa (140 psi). The vessel was then heated at 90° C. for 3 days before cooling and release of the pressure. The reaction mixture was concentrated in vacuo and the residue taken up in 1N sodium hydroxide solution (100 ml). The mixture was washed with ethyl acetate (2×100 ml) then acidified to pH4 with glacial acetic acid. The resulting mixture was extracted with dichloromethane (2×100 ml), the combined organic extracts dried over magnesium sulfate, filtered and the solvent removed in vacuo. Co-evaporation from toluene to remove excess acetic acid gave the title compound (contaminated with 30% 2-acetyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid) as a white solid (0.66 g).

Workup

  1. customThe vessel was purged with carbon monoxide 3 times
  2. additionbefore being charged with carbon monoxide at 965 kPa (140 psi)
  3. temperaturebefore cooling
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. washThe mixture was washed with ethyl acetate (2×100 ml)
  6. extractionThe resulting mixture was extracted with dichloromethane (2×100 ml)
  7. dry with materialthe combined organic extracts dried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customCo-evaporation from toluene
  11. customto remove excess acetic acid

Sources & evidence

ORD record
ord-715d0c2fbad24c3d84b852cae145ea34
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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