Hydrochloric Acid → HCID 86689261, compound

HRID 1409521Notes

Reaction equation

HRID 1409521 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13]COCC.[Br:18][C:19]1[CH:20]=[C:21]2[C:31](=[CH:32][CH:33]=1)[O:30][C:24]1[CH:25]=[N:26][C:27]([Cl:29])=[CH:28][C:23]=1[C:22]2=[N:34]S(C(C)(C)C)=O.Cl.O1CCOCC1>C1COCC1>[NH2:34][C:22]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[C:23]2[CH:28]=[C:27]([Cl:29])[N:26]=[CH:25][C:24]=2[O:30][C:31]2[C:21]1=[CH:20][C:19]([Br:18])=[CH:33][CH:32]=2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 65369187186521-04-0HCID 86689260HCID 86689260, compoundHCID 178418339Butyllithium

Product 1

HCID 86689261HCID 86689261, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Butyllithium solution, 2.5m in hexanes (1.257 mL, 3.14 mmol) was added dropwise to a solution of 1-bromo-2-(ethoxymethoxy)benzene (0.726 g, 3.14 mmol) in THF 20 mL at −78° C. The reaction was stirred for 25 min. Then N-(7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide (1.0 g, 2.417 mmol) in THF was added. The reaction was warmed up to RT and stirred for an hour. The reaction was quenched with saturated ammonium chloride solution and extracted with EtOAc. The organic phase was separated and washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography with gradient of 15-50% EtOAc/Hexane. The resulting material was dissolved in dry MeOH 10 mL and cooled in an ice bath. Hydrochloric acid, 4.0M solution in 1,4-dioxane (20 mL, 80 mmol) was added and mixture was stirred at RT for 4 h. The reaction was quenched with 10% sodium carbonate solution and extracted with DCM three times. The combined organic layers were washed with brine, dried on sodium sulfate, filtered and concentrated to give the desired product which was used without further purificationMS m/z=402.8 [M+H]+.

Workup

  1. stirringstirred for an hour
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. extractionextracted with EtOAc
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by column chromatography with gradient of 15-50% EtOAc/Hexane
  10. dissolutionThe resulting material was dissolved in dry MeOH 10 mL
  11. temperaturecooled in an ice bath
  12. stirringmixture was stirred at RT for 4 h
  13. customThe reaction was quenched with 10% sodium carbonate solution
  14. extractionextracted with DCM three times
  15. washThe combined organic layers were washed with brine
  16. customdried on sodium sulfate
  17. filtrationfiltered
  18. concentrationconcentrated

Sources & evidence

ORD record
ord-4f4b502762bd441b921772680e756662
Source dataset
uspto-grants-2014_12
Patent number
US08921363B2

Reaction notes

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