Diisopropylamine → (1-[4-(4-oxo-2-phenyl-8-trimethylsilanylethynyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

HRID 1037400Notes

Reaction equation

HRID 1037400 reaction equation
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(NC(C)C)(C)C.[C:21]([O:25][C:26](=[O:56])[NH:27][C:28]1([C:32]2[CH:37]=[CH:36][C:35]([C:38]3[C:47](=[O:48])[C:46]4[C:41](=[C:42](Br)[CH:43]=[CH:44][CH:45]=4)[O:40][C:39]=3[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[CH:34][CH:33]=2)[CH2:31][CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22].[CH3:57][Si:58]([C:61]#[CH:62])([CH3:60])[CH3:59]>C1(C)C=CC=CC=1.[Cu]I.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl>[C:21]([O:25][C:26](=[O:56])[NH:27][C:28]1([C:32]2[CH:37]=[CH:36][C:35]([C:38]3[C:47](=[O:48])[C:46]4[C:41](=[C:42]([C:62]#[C:61][Si:58]([CH3:60])([CH3:59])[CH3:57])[CH:43]=[CH:44][CH:45]=4)[O:40][C:39]=3[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[CH:34][CH:33]=2)[CH2:31][CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 67067700{1-[4-(8-Bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 67067912(1-[4-(4-oxo-2-phenyl-8-trimethylsilanylethynyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 1140TolueneSolvent

Procedure

Copper(I) iodide (1 mg, 0.005 mmol) and bis(benzonitrile)dichloro palladium(II) (2 mg, 0.005 mmol) were dissolved in toluene (1 mL) with stirring. Tri-tert-butylphosphine (2 mg, 0.01 mmol), diisopropylamine (0.017 ml, 0.118 mmol), {1-[4-(8-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (50 mg, 0.091 mmol) and (trimethylsilyl)acetylene (0.015 mL, 0.109 mmol) were added, the vial was sealed, and reaction mixture was stirred at RT under an atmosphere of argon for 3 h. The mixture was concentrated in vacuo and the resultant residue subjected to flash chromatography (SiO2, gradient 0 to 10% ethyl acetate in DCM) to afford the title compound as a white solid (51 mg, 100%). LCMS (Method G): RT=5.30 min, [M+H]+=564.

Workup

  1. customthe vial was sealed
  2. customreaction mixture
  3. stirringwas stirred at RT under an atmosphere of argon for 3 h
  4. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-b3d82f3a7f774d3d904ad733517b19b2
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

Loading…