Ethyl Acetate → HCID 66779473, compound

HRID 2168154Notes

Reaction equation

HRID 2168154 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([Si](C)(C)C)[O:10][C:3]=12.[F-].[K+].[I:17]C1CC(=O)NC1=O.C(OC(=O)C)C>C(#N)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([I:17])[O:10][C:3]=12

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 522689Potassium FluorideHCID 22065879HCID 22065879, compoundHCID 594273397-Chloro-2-(trimethylsilyl)furo[3,2-b]pyridine

Product 1

HCID 66779473HCID 66779473, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

7-Chloro-2-trimethylsilanyl-furo[3,2-b]pyridine (185 g, 0.23 mol) is dissolved in ACN under nitrogen atmosphere. Then KF (47.6 g, 0.82 mol) and Iodosuccinimide (553.1 g, 0.25 mol) are added. The reaction mixture is stirred at 60° C. for 14 h and then cooled to room temperature. To the reaction mixture is added acetic acid ethyl ester (5 l) and water (5 l). The organic layer is separated, washed with sodiumthiosulfate (5 l) solution, then extracted with NaHCO3 solution and washed with brine. The organic layer is dried over Na2SO4. The drying agent is filtered and the solvent is removed in vacuum; yield: 133 g 7-chloro-2-iodo-furo[3,2-b]pyridine; HPLC/MS: 2.34 min, [M+H]=280;

Workup

  1. temperaturecooled to room temperature
  2. customThe organic layer is separated
  3. washwashed with sodiumthiosulfate (5 l) solution
  4. extractionextracted with NaHCO3 solution
  5. washwashed with brine
  6. dry with materialThe organic layer is dried over Na2SO4
  7. filtrationThe drying agent is filtered
  8. customthe solvent is removed in vacuum
  9. custom2.34 min, [M+H]=280

Sources & evidence

ORD record
ord-9d7554267dca45fd81ec5128397f0137
Source dataset
uspto-grants-2015_06
Patent number
US09045493B2

Reaction notes

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