Ethyl bromoacetate → HCID 54678064, compound

HRID 1244142Notes

Reaction equation

HRID 1244142 reaction equation
[OH:1][C:2]1[C:3]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[OH:26])=[CH:16][CH:15]=3)=[CH:12][S:11][C:4]=2[NH:5][C:6](=[O:10])[C:7]=1[C:8]#[N:9].C(=O)([O-])[O-].[K+].[K+].C([O:35][C:36](=[O:39])[CH2:37]Br)C>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:8]([C:7]1[C:6](=[O:10])[NH:5][C:4]2[S:11][CH:12]=[C:13]([C:14]3[CH:15]=[CH:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH2:37][C:36]([OH:39])=[O:35])=[CH:18][CH:19]=3)[C:3]=2[C:2]=1[OH:1])#[N:9]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 54708532A-769662

Product 1

HCID 54678064HCID 54678064, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

To solution of 4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.090 g, 0.25 mmol) in acetone (20 mL) was added potassium carbonate (0.14 g, 1 mmol) and tetrabutyl-ammonium iodide (0.005 g, 0.5 mmol) at room temperature. After stirring for 30 min, bromo-acetic acid ethyl ester (0.083 g, 0.5 mmol) was then added into the reaction mixture and stirred for 16 h. The solvent was removed in vacuo, diluted with water (15 mL), extracted with ethyl acetate (3×30 mL), organics extracts washed with brine (15 mL), dried (Na2SO4), concentrated and purified on a RP-HPLC system. The title compound was one of the three reaction products that were purified. MS (ESI) m/e 416.9 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 12.44 (br s, 1H), 7.57 (d, J=7.98, 2H), 7.46 (d, J=8.29, 2H), 7.36–7.30 (m, 2H), 7.08–6.98 (m, 3H), 4.74 (s, 2H).

Workup

  1. stirringstirred for 16 h
  2. customThe solvent was removed in vacuo
  3. additiondiluted with water (15 mL)
  4. extractionextracted with ethyl acetate (3×30 mL)
  5. washorganics extracts washed with brine (15 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified on a RP-HPLC system
  9. customone of the three reaction products that
  10. customwere purified

Sources & evidence

ORD record
ord-1d1ab91faa7f492c86f13a4415c7a9ee
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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