Sulfoxonium, trimethyl-, iodide (1:1) → HCID 67111692, compound

HRID 1177512Notes

Reaction equation

HRID 1177512 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:28]([N:41]=2)=[N:29][C:30]([C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH2:34])=[CH:31][CH:32]=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:28]([N:41]=2)=[N:29][C:30]([C:33]2([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH2:2][CH2:34]2)=[CH:31][CH:32]=3)=[C:21]([F:42])[CH:20]=1

Participants

6

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 67111831HCID 67111831, compound

Product 1

HCID 67111692HCID 67111692, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Trimethylsulfoxonium iodide (0.16 g, 0.72 mmol) and potassium tert-butoxide (0.080 g, 0.72 mmol) were combined in 1.5 mL DMSO to give a clear solution. A slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylvinyl)thiazolo[4,5-b]pyridine (0.200 g, 0.48 mmol) in 4 mL THF was added dropwise, rinsing with 1 mL THF. The reaction mixture was stirred overnight, and was then quenched with sat'd aq. NH4Cl and EtOAc. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo. The material was treated with DCM and passed through a Redi-Sep® pre-packed silica gel column (12 g) using 0-70% EtOAc/hexane. The product-containing fractions were concentrated to afford 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclopropyl)thiazolo[4,5-b]pyridine as a pale yellow solid. MS (ESI) m/z: calculated: 432.1; Observed: 433.1 (M++1).

Workup

  1. customto give a clear solution
  2. washrinsing with 1 mL THF
  3. customwas then quenched with sat'd aq. NH4Cl and EtOAc
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionThe material was treated with DCM
  9. concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record
ord-e336f7d4b7f94b17b50691839318c540
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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