Ethyl Acetate → HCID 15290716, compound

HRID 1018966Notes

Reaction equation

HRID 1018966 reaction equation
[Br:1][C:2]1[C:6]2=[N:7][C:8]([C:11]([OH:13])=[O:12])=[CH:9][CH:10]=[C:5]2[S:4][CH:3]=1.S1C2C(=NC(C(OC)=O)=CC=2)C=[CH:15]1.BrBr.CCOC(C)=O>C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:6]2=[N:7][C:8]([C:11]([O:13][CH3:15])=[O:12])=[CH:9][CH:10]=[C:5]2[S:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24408BromineHCID 18398665HCID 18398665, compoundHCID 18398675HCID 18398675, compound

Product 1

HCID 15290716HCID 15290716, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

3-Bromo-thieno[3,2-b]pyridine-5-carboxylic acid (Gronowitz, S.; Westerlund, C.; Hornfeldt, A. -B.; Acta Chem Scand. 29, 233, 1975) was esterified to the corresponding methyl ester. To a solution of the resulting methyl thieno[3,2-b]pyridine-5-carboxylate 9.7 g, 50.2 mmol) in CHCl3 at 0° C. was added a solution of bromine (16 g, 100.4 mmol) in CCl4 (150 mL) dropwise. The mixture was warmed to r.t. and stirred for 72 h. EtOAc (750 mL) was added. The mixture was washed with NaHSO3, dried (anhyd. MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel to give 2.84 g (21%) of the title compound and 5.5 g of starting material.

Workup

  1. washThe mixture was washed with NaHSO3
  2. dry with materialdried (anhyd. MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5fbf7ad0daab434489415871496d1be4
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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