Potassium Carbonate → HCID 11725334, compound

HRID 1724670Notes

Reaction equation

HRID 1724670 reaction equation
[Mg:1].[Br:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.[N:8]12[CH2:15][CH2:14][CH:11]([CH2:12][CH2:13]1)[C@@H:10]([NH:16][C:17](=[O:25])[C:18](=[O:24])[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH2:9]2.[Cl-].[NH4+].C([O-])([O-])=O.[K+].[K+]>C1COCC1.CCOCC>[S:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[Mg:1][Br:2].[N:8]12[CH2:15][CH2:14][CH:11]([CH2:12][CH2:13]1)[C@@H:10]([NH:16][C:17](=[O:25])[C:18]([OH:24])([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)[CH2:9]2

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 138512-BromothiopheneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 67547547HCID 67547547, compound

Product 2

HCID 11725334HCID 11725334, compoundHCID 178418438HCID 178418438, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-thienylmagnesium bromide was prepared from 2.27 g (0.094 mol) of magnesium and 15.4 g (0.094 mol) of 2-bromothiophene in 150 ml of THF. This solution was added to a solution of 11.34 g (0.043 mol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-2-oxo-2-thien-2-ylacetamide (Intermediate I-1) in 120 ml of THF. The mixture was stirred at room temperature for one hour, refluxed for one hour, cooled and treated with a saturated solution of ammonium chloride. The solution obtained was basified with a K2CO3 solution and extracted with CH2Cl2. The organic layer was washed with water and brine, dried over Na2SO4 and treated with activated carbon. The solution obtained was filtered trough Celite and solvents were evaporated to give a solid that was treated with ether and filtered to give 8.77 (58.5%) of the title product.

Workup

  1. temperaturerefluxed for one hour
  2. temperaturecooled
  3. customThe solution obtained
  4. extractionextracted with CH2Cl2
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. additiontreated with activated carbon
  8. customThe solution obtained
  9. filtrationwas filtered trough Celite and solvents
  10. customwere evaporated
  11. customto give a solid
  12. filtrationfiltered

Sources & evidence

ORD record
ord-7a0dafc93f844426998f8db4ed5b793c
Source dataset
uspto-grants-2009_02
Patent number
US07488735B2

Reaction notes

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