Sulfoxonium, trimethyl-, iodide (1:1) → HCID 118235473, compound

HRID 626947Notes

Reaction equation

HRID 626947 reaction equation
[I-].C[S+](C)(C)=O.[CH3:7]C(C)([O-])C.[K+].[F:13][CH:14]([F:49])[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]1[N:27]2[CH:28]=[C:29]([C:32]3[CH:33]=[N:34][C:35]([C:38]4[CH2:43][CH2:42][CH:41]([C:44]([O:46][CH3:47])=[O:45])[CH2:40][CH:39]=4)=[N:36][CH:37]=3)[CH:30]=[CH:31][C:26]2=[N:25][C:24]=1[CH3:48]>CS(C)=O.C(Cl)Cl>[F:49][CH:14]([F:13])[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]1[N:27]2[CH:28]=[C:29]([C:32]3[CH:33]=[N:34][C:35]([C:38]45[CH2:7][CH:43]4[CH2:42][CH:41]([C:44]([O:46][CH3:47])=[O:45])[CH2:40][CH2:39]5)=[N:36][CH:37]=3)[CH:30]=[CH:31][C:26]2=[N:25][C:24]=1[CH3:48]

Participants

6

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 89923969HCID 89923969, compound

Product 1

HCID 118235473HCID 118235473, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of trimethylsulfoxonium iodide (176 mg, 0.79 mmol) and potassium tert-butoxide (85 mg, 0.75 mmol) in DMSO (2 mL) was stirred at 50° C. for 45 minutes. A solution of methyl 4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]cyclohex-3-ene-1-carboxylate (prepared in an analogous manner to that described for Example 39, 100 mg, 0.2 mmol) in DMSO (2 mL) was added and the mixture was stirred at 50° C. for 4 h, then at room temperature for 3 days. The reaction mixture was diluted with DCM (10 mL) and washed with water (3×3 mL). The aqueous washes were combined and further extracted with DCM (2×3 mL). The organic extracts were combined, dried over sodium sulfate and evaporated. The resulting crude brown residue was diluted with DCM (3 mL) and washed with 1N aqueous NaOH solution (3×1 mL). The organic phase was dried over sodium sulfate and evaporated. The resulting pale brown residue was purified by preparative TLC, eluting with 1% MeOH in DCM, to afford the title compound (38.3 mg, 37%) as an off-white solid. Method B HPLC-MS: MH+ m/z 519, RT 1.80 minutes.

Workup

  1. additionwas added
  2. waitat room temperature for 3 days
  3. washwashed with water (3×3 mL)
  4. extractionfurther extracted with DCM (2×3 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. additionThe resulting crude brown residue was diluted with DCM (3 mL)
  8. washwashed with 1N aqueous NaOH solution (3×1 mL)
  9. dry with materialThe organic phase was dried over sodium sulfate
  10. customevaporated
  11. customThe resulting pale brown residue was purified by preparative TLC
  12. washeluting with 1% MeOH in DCM

Sources & evidence

ORD record
ord-d5277d8b635848709990aee11d4caea4
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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