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 2366129Notes

Reaction equation

HRID 2366129 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-d2d54353b4324339917ff7aee2afe5c6
Source dataset
uspto-grants-2014_04
Patent number
US08697732B2

Reaction notes

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