Triethylamine → N-(4-(4-oxo-7-((trimethylsilyl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide

HRID 1188260Notes

Reaction equation

HRID 1188260 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:28])[C:12]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=3)=[CH:13][O:14]2)=[CH:9][CH:8]=1)(=O)=O.[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[O:28]=[C:11]1[C:10]2[C:15](=[CH:16][C:7]([C:36]#[C:35][Si:32]([CH3:34])([CH3:33])[CH3:31])=[CH:8][CH:9]=2)[O:14][CH:13]=[C:12]1[C:17]1[CH:18]=[CH:19][C:20]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 866950543-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate

Product 1

HCID 86695055N-(4-(4-oxo-7-((trimethylsilyl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate (2.5 g, 5.39 mmol), trimethylsilylacetylene (0.92 ml, 1.2 eq), PdCl2(PPh3)2 (175 mg, 0.05 eq), copper iodide (28.8 mg 0.03 eq), triphenylphosphine (40 mg 0.03 eq) and triethylamine (3.12 ml, 4.0 eq) were combined in dry tetrahydrofuran (10 ml) and heated in microwave for 30 minutes at 85° C. The reaction mixture was partitioned between ethyl acetate and water, the organic phase dried with magnesium sulfate, and solvent removed under reduced pressure. The crude product was heated in acetonitrile, cooled down and the solids were filtered off. This procedure was repeated twice in order to afford N-(4-(4-oxo-7-((trimethylsilyl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialthe organic phase dried with magnesium sulfate, and solvent
  3. customremoved under reduced pressure
  4. temperatureThe crude product was heated in acetonitrile
  5. temperaturecooled down
  6. filtrationthe solids were filtered off

Sources & evidence

ORD record
ord-887945504d6445d8a911b2dba30c79c0
Source dataset
uspto-grants-2014_03
Patent number
US08673966B2

Reaction notes

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