Sulfoxonium, trimethyl-, iodide (1:1) → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylcyclopropyl)thiazolo[4,5-c]pyridine

HRID 1177516Notes

Reaction equation

HRID 1177516 reaction equation
[CH3:1]C(C)([O-])C.[K+].[I-].C[S+](C)(C)=O.[O:13]1[CH2:18][CH2:17][CH2:16][O:15][CH:14]1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[S:26][C:27]3[CH:32]=[C:31]([C:33]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH2:34])[N:30]=[CH:29][C:28]=3[N:41]=2)=[C:21]([F:42])[CH:20]=1>CS(C)=O.C1COCC1>[O:15]1[CH2:16][CH2:17][CH2:18][O:13][CH:14]1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[S:26][C:27]3[CH:32]=[C:31]([C:33]4([C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=5)[CH2:1][CH2:34]4)[N:30]=[CH:29][C:28]=3[N:41]=2)=[C:21]([F:42])[CH:20]=1

Participants

6

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 671127762-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylvinyl)thiazolo[4,5-c]pyridine

Product 1

HCID 671116612-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylcyclopropyl)thiazolo[4,5-c]pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a clear solution of potassium tert-butoxide (0.201 g, 1.79 mmol) and trimethylsulfoxonium iodide (0.394 g, 1.79 mmol) in 5 mL DMSO was added a cloudy mixture of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylvinyl)thiazolo[4,5-c]pyridine (0.500 g, 1.19 mmol) in 20 mL THF rapidly. After 4 h, the reaction mixture was partitioned between EA and sat'd aq NH4Cl, and the organic layer was washed with water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting material was taken up in DCM and was filtered. The filtrate was collected and adsorbed onto 2 g silica gel and dried in vacuo. The resulting material was purified by silica gel chromatography, 40 g, 0-100% EA/hexanes to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylcyclopropyl)thiazolo[4,5-c]pyridine as a white solid. MS (ESI) m/z: calculated: 432.1; Observed: 433.0 (M++1).

Workup

  1. customthe reaction mixture was partitioned between EA
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationwas filtered
  7. customThe filtrate was collected
  8. customdried in vacuo
  9. customThe resulting material was purified by silica gel chromatography, 40 g, 0-100% EA/hexanes

Sources & evidence

ORD record
ord-8aa690985faa49a8921f08562d66942f
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

Loading…