Dimethylformamide → HCID 22502962, compound

HRID 1007036Notes

Reaction equation

HRID 1007036 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:11]=[CH:10][S:9][C:5]2=[C:6](Br)[N:7]=1.C(N1[CH2:19][CH2:18][CH2:17][CH2:16]C1)C.[C:20](=O)([O-])[O-].[K+].[K+].[CH3:26][N:27]([CH3:30])C=O>>[CH2:17]([CH:18]1[CH2:19][CH2:30][N:27]([C:6]2[N:7]=[C:2]([Br:1])[CH:3]=[C:4]3[CH:11]=[CH:10][S:9][C:5]=23)[CH2:26][CH2:20]1)[CH3:16]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 13007N-EthylpiperidineHCID 22503283HCID 22503283, compound

Product 1

HCID 22502962HCID 22502962, compound

Procedure

5,7-Dibromothieno[2,3-c]pyridine (2.04 g), 1-ethylpiperidine (0.95 g) and potassium carbonate (2.0 g) were reacted in N,N-dimethylformamide (15 ml) at 70° C. for 2 hr. The reaction mixture was evaporated, and the resulting residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water and brine, and dried over magnesium sulfate. The resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol system), to give 7-(4-ethylpiperidin-1-yl)-5-bromothieno[2,3-c]pyridine (1.95 g) as a brown oil.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe resulting residue was partitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol system)

Sources & evidence

ORD record
ord-97afcc4c300742458bb7d7b2a6b68a81
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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