Water → HCID 57659534, compound

HRID 217174Notes

Reaction equation

HRID 217174 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([O:9][C:10]([C:12]1[O:20][C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[C:13]=1[OH:21])=[O:11])[CH3:8].[CH:22]1[CH:27]=[CH:26][C:25]([CH2:28]Br)=[CH:24][CH:23]=1.O>CN(C=O)C>[CH2:7]([O:9][C:10]([C:12]1[O:20][C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[C:13]=1[O:21][CH2:28][C:25]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1)=[O:11])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 54695711HCID 54695711, compound

Product 1

HCID 57659534HCID 57659534, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 (2.34 g, 17.0 mmol) was added to a stirred solution of 3-hydroxyfuro[3,2-c]pyridine-2-carboxylic acid ethyl ester (1.76 g, 8.5 mmol) in DMF (40 mL). After 5 min, BnBr (1.25 mL, 10.6 mmol) was added, then the mixture was stirred for 16 h, before being poured into H2O and extracted with EtOAc (3×). The combined organic extracts were washed with brine, before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (EtOAc) yielded the title compound: m/z (ES+)=298.0 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialbefore being dried (MgSO4)
  4. filtrationFiltration, solvent evaporation, and column chromatography (EtOAc)

Sources & evidence

ORD record
ord-d9a9ac852fb1474ba0a16f0eab83a498
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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