2,3-Dichloropyridine → HCID 57979781, compound

HRID 1868030Notes

Reaction equation

HRID 1868030 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C@@H:19]([CH3:20])[CH2:18][NH:17][CH2:16][C@@H:15]2[CH3:21])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1.C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]2[C@@H:19]([CH3:20])[CH2:18][N:17]([C:23]3[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:16][C@@H:15]2[CH3:21])(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 169882,3-DichloropyridineHCID 81531DiisopropylethylamineHCID 57979779HCID 57979779, compound

Product 1

HCID 57979781HCID 57979781, compoundYield 27.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2S,6S)-1-[(4-tert-butylphenyl)sulfonyl]-2,6-dimethylpiperazine (120 mg, 0.39 mmol) and 2,3-Dichloropyridine (115 mg, 0.78 mmol) in anhydrous 1,4-Dioxane (0.2 mL) was added diisopropylethylamine (0.201 mL, 1.16 mmol). The mixture was subject to microwave irradiation at 200° C. for 1 hour. Reaction was half complete as determined by TLC. The reaction mixture was diluted with ethyl acetate and washed with saturated NH4Cl (aq.), 10% HCl (aq.), water and brine. Organic layer was dried over MgSO4. Solvent evaporation followed by flash column chromatography afforded (2S,6S)-1-[(4-tert-butylphenyl)sulfonyl]-4-(3-chloropyridin-2-yl)-2,6-dimethylpiperazine in 27.7% yield (45 mg) as off white solid.

Workup

  1. customirradiation at 200° C. for 1 hour
  2. customReaction
  3. washwashed with saturated NH4Cl (aq.), 10% HCl (aq.), water and brine
  4. dry with materialOrganic layer was dried over MgSO4
  5. customSolvent evaporation

Sources & evidence

ORD record
ord-f4d19153164c4f35b336329c0bd4abd0
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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