Sulfoxonium, trimethyl-, iodide (1:1) → HCID 89783633, compound

HRID 1055935Notes

Reaction equation

HRID 1055935 reaction equation
[CH3:1]C(C)([O-])C.[K+].[I-].C[S+](C)(C)=O.[C:13]1([C:19]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[C:24]([C:31]4[NH:39][C:38]5[CH2:37][CH2:36][NH:35][C:34](=[O:40])[C:33]=5[CH:32]=4)[CH:25]=[CH:26][CH:27]=3)[N:22]=2)=[CH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CS(C)=O.Cl>[C:13]1([C:19]2([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[C:24]([C:31]5[NH:39][C:38]6[CH2:37][CH2:36][NH:35][C:34](=[O:40])[C:33]=6[CH:32]=5)[CH:25]=[CH:26][CH:27]=4)[N: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 89784303HCID 89784303, compound

Product 1

HCID 89783633HCID 89783633, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
25 °C

Procedure

A mixture of potassium tert-butoxide (18.42 mg, 0.164 mmol) and trimethylsulfoxonium iodide (36.1 mg, 0.164 mmol) in anhydrous DMSO (0.5 mL) was stirred under argon at 25° C. for 10 min, providing a colorless solution. A solution of 2-(2-(1-phenylvinyl)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 113; 30 mg, 0.082 mmol) in DMSO (1.0 mL) was added (dropwise, over 2 min), and the resulting solution was stirred at 25° C. for 30 min. The reaction solution was diluted with LON aq. HCl (0.1 mL), then partitioned between DCM (50 mL) and water (20 mL). The aq. layer was extracted with additional DCM (20 mL), and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-10% MeOH/DCM) furnished 2-(2-(1-phenylcyclopropyl)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (18.8 mg, 0.050 mmol, 60% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.49 (1H, br. s.), 8.08 (1H, dd, J=7.4, 1.0 Hz), 8.00 (1H, d, J=8.6 Hz), 7.57 (1H, d, J=7.2 Hz), 7.44-7.50 (3H, m), 7.42 (2H, t, J=7.3 Hz), 7.33-7.38 (1H, m), 7.19 (1H, d, J=2.0 Hz), 7.07 (1H, d, J=8.8 Hz), 5.40 (1H, br. s.), 3.63 (2H, td, J=6.8, 2.2 Hz), 2.85 (2H, t, J=6.9 Hz), 1.68-1.72 (2H, m), 1.55-1.60 (2H, m). m/z (ESI, +ve) 380.1 (M+H)+.

Workup

  1. customproviding a colorless solution
  2. stirringwas stirred at 25° C. for 30 min
  3. custompartitioned between DCM (50 mL) and water (20 mL)
  4. extractionThe aq. layer was extracted with additional DCM (20 mL)
  5. dry with materialthe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customChromatographic purification of the residue (silica gel, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-c638cd67ee18420b95ee881bbbe60903
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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