(Triethylsilyl)acetylene → HCID 86712310, compound

HRID 592428Notes

Reaction equation

HRID 592428 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:13])([CH3:12])[C:9]([NH2:11])=[O:10].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[CH2:32]([Si:34]([C:39]#[CH:40])([CH2:37][CH3:38])[CH2:35][CH3:36])[CH3:33]>CN(C=O)C.[Cu]I.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>[CH3:12][C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:33]#[C:32][Si:34]([CH2:39][CH3:40])([CH2:37][CH3:38])[CH2:35][CH3:36])([CH3:13])[C:9]([NH2:11])=[O:10]

Participants

7

Reactant 3

HCID 637947(Triethylsilyl)acetyleneHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 10824050HCID 10824050, compound

Product 1

HCID 86712310HCID 86712310, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
65 °C

Procedure

A mixture of 2-(2-bromophenyl)-2-methylpropanamide A34 (0.196 g, 0.810 mmol), CuI (0.008 g, 0.040 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.012 g, 0.040 mmol), PdCl2(PPh3)2 (0.028 g, 0.040 mmol) and (triethylsilyl)acetylene (0.174 mL, 0.971 mmol) in DMF (5 mL) was bubbled with N2 for 10 minutes. Et3N (5 mL) was added and the mixture was stirred under nitrogen at 65° C. for 4 hours. The mixture was cooled and the volatiles were removed in vacuo. The dark brown residue was adsorbed onto silica and purified by column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A35 as a brown solid (0.116 g, 48%). LCMS-D: rt 3.84 min; m/z 302 [M+H]+.

Workup

  1. customwas bubbled with N2 for 10 minutes
  2. additionEt3N (5 mL) was added
  3. temperatureThe mixture was cooled
  4. customthe volatiles were removed in vacuo
  5. custompurified by column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-7facef39fcbd42e9b609db24404db5fa
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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