Sodium hydride → HCID 86705061, compound

HRID 1477926Notes

Reaction equation

HRID 1477926 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:21]2[C:29]3[C:24](=[C:25]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22]2)([CH2:19][CH3:20])[CH:17]=[O:18])=[CH:12][CH:11]=1>CS(C)=O.C1COCC1>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:21]2[C:29]3[C:24](=[C:25]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22]2)([CH:17]2[CH2:4][O:18]2)[CH2:19][CH3:20])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 86705043HCID 86705043, compound

Product 1

HCID 86705061HCID 86705061, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of NaH (41 mg, 0.764 mmol, 60% in oil) in DMSO (15 mL) at 0° C. was added trimethylsulfoxonium iodide (235 mg, 1.07 mmol) divided into several portions. The mixture was stirred at room temperature until the mixture became clear. To the solution of tert-butyl 1-(2-(4-chlorophenyl)-1-oxobutan-2-yl)-1H-indol-4-ylcarbamate (210 mg, 0.509 mmol), as described in Example 21 Step B, in THF (15 mL) was added the upper solution dropwise at 0° C. Then the mixture was stirred at room temperature for 2 h. The reaction was quenched with saturated ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with brine (15 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography with PE/EA (10/1 to 3/1, v/v) to afford the title compound as a colorless solid. LC/MS m/z=448.9[M+Na]+.

Workup

  1. additionwas added the upper solution dropwise at 0° C
  2. stirringThen the mixture was stirred at room temperature for 2 h
  3. customThe reaction was quenched with saturated ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine (15 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by silica gel chromatography with PE/EA (10/1 to 3/1

Sources & evidence

ORD record
ord-81db536f8a9b4c4fad25e1402e436574
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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