Sodium hydride → HCID 118098781, compound

HRID 708915Notes

Reaction equation

HRID 708915 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[C:9]([O:13][C:14]([NH:16][C:17]1[CH:18]=[CH:19][C:20]([C:33]([C:35]#[N:36])=[CH2:34])=[C:21]([CH:32]=1)[CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:15])([CH3:12])([CH3:11])[CH3:10]>CS(C)=O>[C:9]([O:13][C:14]([NH:16][C:17]1[CH:18]=[CH:19][C:20]([C:33]2([C:35]#[N:36])[CH2:4][CH2:34]2)=[C:21]([CH:32]=1)[CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:15])([CH3:10])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 118098780HCID 118098780, compound

Product 1

HCID 118098781HCID 118098781, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a suspension of sodium hydride (0.019 g, 0.795 mmol) in DMSO (2 mL), was added trimethylsulfoxonium iodide (0.191 g, 0.867 mmol). The mixture was stirred at rt for 2 h. To the resultant clear solution was added to a solution of 36F (0.280 g, 0.723 mmol) in DMSO (2 mL) to give a yellow solution. The mixture was stirred at rt for 1 h, then at 60° C. for 5 h. Reaction mixture was quenched with sat. NH4Cl (10 mL), extracted with EtOAc (4×25 mL). Combined organic phase was washed with water (2×25 mL), brine (1×25 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified by flash chromatography (0-40% EtOAc/hexanes) to give 36G (0.144 g, 0.359 mmol, 49.6% yield) as a colorless syrup. MS (ESI) m/z: 402.2 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.33-7.58 (1H, m), 7.23 (1H, d, J=8.28 Hz), 6.91-7.11 (1H, m), 6.60-6.79 (1H, m), 4.71 (2H, br. s.), 2.82-2.98 (3H, m), 1.66 (2H, br. s.), 1.37-1.58 (18H, m), 1.19-1.32 (2H, m).

Workup

  1. customto give a yellow solution
  2. stirringThe mixture was stirred at rt for 1 h
  3. waitat 60° C. for 5 h
  4. customReaction mixture
  5. customwas quenched with sat. NH4Cl (10 mL)
  6. extractionextracted with EtOAc (4×25 mL)
  7. washCombined organic phase was washed with water (2×25 mL), brine (1×25 mL)
  8. dry with materialdried (Na2SO4)
  9. customEtOAc was removed under reduced pressure
  10. customthe residue was purified by flash chromatography (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7e8bed368e9b4fdcb7e96b6f0e20b254
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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