Sulfoxonium, trimethyl-, iodide (1:1) → 5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-carboxylic acid

HRID 1177402Notes

Reaction equation

HRID 1177402 reaction equation
[CH3:1]C([O-])(C)C.[K+].[I-].C[S+](C)(C)=O.[C:13]1([C:19]([C:21]2[N:26]=[C:25]3[S:27][C:28]([C:30]([O-:32])=[O:31])=[N:29][C:24]3=[CH:23][CH:22]=2)=[CH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Na+]>CS(C)=O.Cl>[C:13]1([C:19]2([C:21]3[N:26]=[C:25]4[S:27][C:28]([C:30]([OH:32])=[O:31])=[N:29][C:24]4=[CH:23][CH:22]=3)[CH2:1][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 67111612HCID 67111612, compound

Product 1

HCID 671116745-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
25 °C

Procedure

Potassium 2-methylpropan-2-olate (0.66 g, 5.9 mmol) was dissolved in anhydrous DMSO (19.5 mL) under argon. Trimethylsulfoxonium iodide (1.3 g, 5.9 mmol) was added to the resulting solution in one portion. After 10 min, this dissolved, and the resulting clear solution was added via cannula (over ˜2 min) to a suspension of sodium 5-(1-phenylvinyl)thiazolo[5,4-b]pyridine-2-carboxylate (1.19 g, 3.9 mmol) in DMSO (5 mL) at 25° C. The resulting solution was stirred at 25° C. for 1 h. The reaction solution was then diluted with 1.0N HCl (8.0 mL) and partitioned between dichloromethane (400 mL) and water (400 mL). The organic layer was separated, and the aqueous layer was extracted with additional dichloromethane (200 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to afford crude 5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-carboxylic acid as a yellow oil. MS (ESI) m/z: Calculated: 296.1; Observed: 297.0 (M++1).

Workup

  1. custompartitioned between dichloromethane (400 mL) and water (400 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with additional dichloromethane (200 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ceafd9b22cc747369880d343e9111e9d
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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