Tetrafluoroborate → 1-(2-((Trimethylsilyl)ethynyl)phenyl)cyclopropanecarboxamide

HRID 592351Notes

Reaction equation

HRID 592351 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:11]([NH2:13])=[O:12])[CH2:10][CH2:9]1.[C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])#[CH:15].F[B-](F)(F)F>CN(C=O)C.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>[CH3:17][Si:16]([C:14]#[C:15][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:11]([NH2:13])=[O:12])[CH2:10][CH2:9]1)([CH3:19])[CH3:18]

Participants

7

Reactant 3

HCID 26255TetrafluoroborateHCID 66111TrimethylsilylacetyleneHCID 867122741-(2-Iodophenyl)cyclopropanecarboxamide

Product 1

HCID 867122751-(2-((Trimethylsilyl)ethynyl)phenyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2-iodophenyl)cyclopropanecarboxamide (I11) (1.53 g, 85.3 mmol), ethynyltrimethylsilane (1.05 mL, 7.46 mmol), PdCl2(PPh3)2 (0.037 g, 0.053 mmol), t-Bu3PH.BF4 (0.031 g, 0.11 mmol) and copper(I) iodide (0.020 g, 0.11 mmol) in DMF (10 mL) was stirred under a nitrogen atmosphere at 50° C. for 26 hours. The volatiles were evaporated in vacuo and the resulting black residue was purified using silica gel column chromatography (CombiFlash Rf, 24 g SiO2 Cartridge, 5-20% EtOAc in cyclohexane) to give the title compound I12 as a dark yellow amorphous solid (1.09 g, 79%); 1H NMR (300 MHz, CDCl3) δ 7.52 (d, J=7.1 Hz, 1H), 7.26-7.50 (m, 3H), 5.26 (brs, 2H), 1.72 (dq, J=4.1 Hz, 2H) 1.16 (dq, J=3.9 Hz, 2H), 0.26 (s, 9H). LCMS-B: rt 7.446 min; m/z 258 [M+H]+.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customthe resulting black residue was purified

Sources & evidence

ORD record
ord-d41f239dfad74e26b88a759b15982ea7
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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