Sulfoxonium, trimethyl-, iodide (1:1) → Methyl 2-(1-methylcyclopropyl)quinoline-6-carboxylate

HRID 2425567Notes

Reaction equation

HRID 2425567 reaction equation
[I-].C[S+](C)(C)=O.[CH3:7]C(C)([O-])C.[K+].[C:13]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:26]([O:28][CH3:29])=[O:27])[CH:22]=2)[N:17]=1)([CH3:15])=[CH2:14]>CS(C)=O.C1COCC1>[CH3:14][C:13]1([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:26]([O:28][CH3:29])=[O:27])[CH:22]=3)[N:17]=2)[CH2:7][CH2:15]1

Participants

6

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 66637151Methyl 2-isopropenylquinoline-6-carboxylate

Product 1

HCID 66636963Methyl 2-(1-methylcyclopropyl)quinoline-6-carboxylateYield 68.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of trimethylsulfoxonium iodide (435 mg, 2.06 mmol) in dimethylsulfoxide (3 ml) and THF (2 ml) was added potassium tert-butoxide (231 mg, 2.06 mmol) in one portion at ambient temperature. After 30 min. at the same temperature, to this (colorless solution) was added a solution of methyl 2-isopropenylquinoline-6-carboxylate (312 mg, 1.37 mmol) in THF (3 ml) at room temperature. The mixture was stirred at room temperature for 40 min then 1 hour at 60° C. The mixture was quenched with water and diluted with ethyl acetate-toluene (8:1) (90 ml). The organic solution was separated and washed with water (×2), brine, dried over sodium sulfate and concentrated in vacuo to crude product. The crude product was purified by column chromatography on silica gel (250 g) with hexane-ethyl acetate (10:1) to furnish the title compound (225 mg, 68%) as a white solid. 1H NMR (270 MHz, CDCl3) δ 0.91-0.98 (2H, m), 1.38-1.45 (2H, m), 1.64 (3H, s), 3.98 (3H, s), 7.42-7.48 (1H, m), 7.97-8.27 (3H, m), 8.50-8.55 (1H, m). MS (ESI): m/z 242.15 [M+H]+.

Workup

  1. custom1 hour
  2. customat 60° C
  3. customThe mixture was quenched with water
  4. additiondiluted with ethyl acetate-toluene (8:1) (90 ml)
  5. customThe organic solution was separated
  6. washwashed with water (×2), brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo to crude product
  9. customThe crude product was purified by column chromatography on silica gel (250 g) with hexane-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-74e1829b2bcc4b9ab1269956579232c3
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

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