Azidotrimethylsilane → HCID 178452580, compound

HRID 1037403Notes

Reaction equation

HRID 1037403 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[C:22]([C:29]#[CH:30])[CH:23]=[CH:24][CH:25]=4)[O:20][C:19]=3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[N:38]([Si](C)(C)C)=[N+:39]=[N-:40]>CO.CN(C=O)C.CCOC(C)=O.[Cu]I>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[C:22]([C:29]5[N:38]=[N:39][NH:40][CH:30]=5)[CH:23]=[CH:24][CH:25]=4)[O:20][C:19]=3[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 86671055{1-[4-(8-ethynyl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 178452580HCID 178452580, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of {1-[4-(8-Ethynyl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (34 mg, 0.069 mmol) in MeOH (0.2 mL) and DMF (1.8 mL) was treated with copper(I) iodide (1 mg, 0.003 mmol) and azido trimethylsilane (0.014 ml, 0.104 mmol). The reaction mixture was the stirred at 100° C. for 3.75 h. The resultant mixture was allowed to cool to RT, diluted with EtOAc, washed with brine. The aqueous extracts were further washed with EtOAc (×2). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 30% EtOAc in DCM) to give the title compound. LCMS (Method G) RT=3.88 min, [M+H]+=535.

Workup

  1. temperatureto cool to RT
  2. washwashed with brine
  3. washThe aqueous extracts were further washed with EtOAc (×2)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04e7ad30103d4dbca6b7fb2a6c74fe12
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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