N-methyl-2-pyrrolidone → 2,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,3,4]oxadiazol-2-yl]-pyridine

HRID 1924834Notes

Reaction equation

HRID 1924834 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[O:9][C:10]([C:13]3[S:20][C:19]([CH3:21])=[C:18]4[C:14]=3[CH2:15][C@H:16]3[C:22]([CH3:24])([CH3:23])[C@H:17]34)=[N:11][N:12]=2)[CH:5]=[C:4]([CH3:25])[N:3]=1.[CH3:26]N1C(=O)CCC1.C[Mg]I>C1COCC1>[CH3:26][C:2]1[CH:7]=[C:6]([C:8]2[O:9][C:10]([C:13]3[S:20][C:19]([CH3:21])=[C:18]4[C:14]=3[CH2:15][C@H:16]3[C:22]([CH3:24])([CH3:23])[C@H:17]34)=[N:11][N:12]=2)[CH:5]=[C:4]([CH3:25])[N:3]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 248756582-Chloro-6-methyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,3,4]oxadiazol-2-yl]-pyridineHCID 178418373HCID 178418373, compound

Product 1

HCID 248756592,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,3,4]oxadiazol-2-yl]-pyridineYield 46.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-chloro-6-methyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,3,4]oxadiazol-2-yl]-pyridine (62.9 mg, 0.17 mmol), Fe(acac)3 (6 mg) and NMP (20 mg) in THF (5 mL) is added a solution of methylmagnesiumiodide in THF (3M, 0.51 mmol) and the mixture is stirred at rt for 15 h. The mixture is quenched with water (30 mL) and extracted with Et2O (2×50 mL). The organic extracts are dried (MgSO4), filtered and evaporated. The residue is purified by TLC (SiO2, EA-hexane) to give 2,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,3,4]oxadiazol-2-yl]-pyridine (28 mg); LC-MS: tR=0.88 min, [M+1]=352.54.

Workup

  1. customThe mixture is quenched with water (30 mL)
  2. extractionextracted with Et2O (2×50 mL)
  3. dry with materialThe organic extracts are dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by TLC (SiO2, EA-hexane)

Sources & evidence

ORD record
ord-47791984c14044fcbbfece3e9c9195c2
Source dataset
uspto-grants-2012_05
Patent number
US08178562B2

Reaction notes

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