Diisopropylethylamine → HCID 86669619, compound

HRID 76167Notes

Reaction equation

HRID 76167 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])[CH3:10])=[CH:4][CH:3]=1.[Si](C#C)([C:20](C)(C)[CH3:21])(C)C.CCN(C(C)C)C(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O.C(Cl)Cl.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>[C:20]([C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])[CH3:10])=[CH:4][CH:3]=1)#[CH:21]

Participants

10

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724141Tetrabutylammonium FluorideHCID 2757281(tert-Butyldimethylsilyl)acetyleneHCID 66610754N-(1-(4-Iodophenyl)propan-2-YL)cyclopropanecarboxamide

Product 1

HCID 86669619HCID 86669619, compound

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 900 mg (2.73 mmol) N-(1-(4-iodophenyl)propan-2-yl)cyclopropanecarboxamide (I52.3) and 0.56 mL (3.01 mmol) (tert-butyldimethylsilyl)acetylene in 5 mL THF at 0° C. are added 0.77 mL (5.48 mmol) DIPEA, 96.1 mg (0.14 mmol) bis(triphenyl-phosphine)dichloropalladium and 53.1 mg (0.28 mmol) CuI, and the reaction mixture is stirred at r.t. over night. The mixture is diluted with water and extracted with DCM (2×). The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel, DCM/MeOH 98/2) to yield the silylated compound. To this substance in DCM are added 949 mg (3.01 mmol) TBAF*3H2O and the mixture is stirred at r.t. for 3 h. The mixture is diluted with water and extracted with DCM. The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, DCM/MeOH 98/2).

Workup

  1. extractionextracted with DCM (2×)
  2. dry with materialThe organic layer is dried with Na2SO4
  3. customthe solvent is removed in vacuo
  4. customThe residue is purified by column chromatography (silica gel, DCM/MeOH 98/2)
  5. customto yield the silylated compound
  6. stirringthe mixture is stirred at r.t. for 3 h
  7. extractionextracted with DCM
  8. dry with materialThe organic layer is dried with Na2SO4
  9. customthe solvent is removed in vacuo
  10. customThe crude product is purified by column chromatography (silica gel, DCM/MeOH 98/2)

Sources & evidence

ORD record
ord-a3d7f4c8de484fc5aaa3b341922fd5d0
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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