Potassium Carbonate → HCID 18428686, compound

HRID 1279637Notes

Reaction equation

HRID 1279637 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)=[C:6]([CH:10]=1)[CH2:7][NH:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].[NH:26]1[CH:30]=[CH:29][N:28]=[N:27]1>[Cu]>[CH3:9][NH:8][CH2:7][C:6]1[CH:10]=[C:2]([N:27]2[N:28]=[CH:29][CH:30]=[N:26]2)[CH:3]=[CH:4][C:5]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18428716HCID 18428716, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 18428686HCID 18428686, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
160 °C

Procedure

The bromide of Example 23 (2.0 g, 6 mmol) was mixed with copper powder (378 mg, 6 mmol) 1,2,3-triazole (ca. 5 g, excess), and potassium carbonate (828 mg, 6 mmol) were heated together at 160° C. for 48 h. After cooling to room temperature the reaction mixture was partitioned between sodium hydroxide (3 M) and ethyl acetate. The organic layer was separated and washed with sodium hydroxide (3 M) (3 x), water, and brine, before being dried (MgSO4) and evaporated. The resulting residue was purified by flash chromatography [SiO2; DCM/ MeOH/ 880 NH3 (97.5:2.5:0.25)] to afford, separately, the 1-substitiuted triazole derivative compound of Example 181 and the 2-substituted isomer compound of Example 182. The hydrochloride salt of each was precipitated by treatment with ethereal hydrochloric acid (1 M solution, excess).

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas partitioned between sodium hydroxide (3 M) and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with sodium hydroxide (3 M) (3 x), water, and brine
  5. dry with materialbefore being dried (MgSO4)
  6. customevaporated
  7. customThe resulting residue was purified by flash chromatography [SiO2; DCM/ MeOH/ 880 NH3 (97.5:2.5:0.25)]
  8. customto afford
  9. customThe hydrochloride salt of each was precipitated by treatment with ethereal hydrochloric acid (1 M solution, excess)

Sources & evidence

ORD record
ord-8330fcf6305a41a28f5129d5e2a32a85
Source dataset
uspto-grants-2002_09
Patent number
US06448293B1

Reaction notes

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