Tetrahydrofuran → HCID 22502706, compound

HRID 1814499Notes

Reaction equation

HRID 1814499 reaction equation
C(N1CCN([C:9]2[C:14]3[CH:15]=[CH:16][S:17][C:13]=3[CH:12]=[C:11]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][CH:19]=3)[N:10]=2)CC1)C.C([Mg]Br)C.[CH2:30]([O:32]CC)[CH3:31].[Cl-].[NH4+].[O:37]1CCCC1>>[O:32]1[CH2:30][CH2:31][O:25][CH:24]1[C:21]1[CH:20]=[CH:19][C:18]([C:11]2[NH:10][C:9](=[O:37])[C:14]3[CH:15]=[CH:16][S:17][C:13]=3[CH:12]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 22502581HCID 22502581, compoundHCID 178467792HCID 178467792, compound

Product 1

HCID 22502706HCID 22502706, compound

Procedure

To a solution of 4-(4-ethylpiperazin-1-yl)-6-(4-formylphenyl)thieno-[3,2-c]pyridine (0.20 g) in tetrahydrofuran (20 ml) was added 3M ethylmagnesium bromide/diethyl ether solution (0.5 ml), and the mixture was reacted at room temperature for 30 min. To the resulting reaction solution was added an aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried. The resulting product was filtered through NH silica gel and washed with ethyl acetate. The filtrate was concentrated, to give 0.17 g of the title compound as white crystals.

Workup

  1. customthe mixture was reacted at room temperature for 30 min
  2. customTo the resulting reaction solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. customdried
  6. filtrationThe resulting product was filtered through NH silica gel
  7. washwashed with ethyl acetate
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2340495bd80d44c9934f62c21c981668
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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