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

HRID 1177524Notes

Reaction equation

HRID 1177524 reaction equation
[I-].[CH3:2][S+](C)(C)=O.CC(C)([O-])C.[K+].[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[C:32]([N:33]=2)=[CH:31][CH:30]=[C:29]([C:34]([CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH2:35])[N:28]=3)=[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[C:32]([N:33]=2)=[CH:31][CH:30]=[C:29]([C:34]2([CH:36]4[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]4)[CH2:2][CH2:35]2)[N:28]=3)=[C:21]([F:42])[CH:20]=1

Participants

6

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 671116042-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-cyclohexylvinyl)thiazolo[5,4-b]pyridine

Product 1

HCID 671118652-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-cyclohexylcyclopropyl)thiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of trimethylsulfoxonium iodide (0.385 g, 1.75 mmol) and potassium tert-butoxide (0.196 g, 1.75 mmol) in 4 mL DMSO was added 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-cyclohexylvinyl)thiazolo[5,4-b]pyridine (0.371 g, 0.874 mmol) rapidly as a solution in THF (8 mL min volume). The reaction mixture became a light purple color. The reaction was sealed and heated to 60° C. After 4 h, the reaction mixture was cooled, quenched with ice and sat'd aq. NH4Cl, diluted with EtOAc and the organic layer was washed with water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting orange oil/solid was purified by silica gel chromatography 40 g, 0-40% EA/hexanes to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-cyclohexylcyclopropyl)thiazolo[5,4-b]pyridine as a white solid. MS (ESI) m/z: calculated: 438.2; Observed: 439.1 (M++1).

Workup

  1. customThe reaction was sealed
  2. temperaturethe reaction mixture was cooled
  3. customquenched with ice
  4. additiondiluted with EtOAc
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting orange oil/solid was purified by silica gel chromatography 40 g, 0-40% EA/hexanes

Sources & evidence

ORD record
ord-51885f3b5159424f9fb8376bd6bb374a
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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