Sodium Thiosulfate → HCID 58574731, compound

HRID 1619317Notes

Reaction equation

HRID 1619317 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[N:7]3[CH2:15][CH:14]([OH:16])[CH2:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[N:7]3[CH2:15][C:14](=[O:16])[CH2:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 58574676HCID 58574676, compound

Product 1

HCID 58574731HCID 58574731, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-8-hydroxy-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one (1 g, 3.4 mmol, 1 equiv) in THF (30 mL) and DCM (20 mL) at 0° C. was added Dess-Martin reagent (2.9 g, 6.8 mmol, 2 equiv). The resulting mixture was stirred at rt for 3 h. After that, 60 mL of aq. Na2S2O3 was added. The mixture was extracted with ethyl acetate (3×100 mL), dried over Na2SO4. After filtration and concentration, 700 mg of the desired product was obtained, which was directly used for the next step without further purification. MS (ESI): 293, 295 (MH+).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-2efdab69314946ab8ad390ee07fcd847
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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