1-(Trimethylsilyl)prop-1-yne → HCID 86667270, compound

HRID 1770892Notes

Reaction equation

HRID 1770892 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.C[Si](C)(C)[C:11]#[C:12][CH3:13].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1(C)C=CC=CC=1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:4]1[CH:3]=[C:2]([C:11]#[C:12][CH3:13])[CH:7]=[CH:6][N:5]=1

Participants

7

Reactant 3

HCID 803631-(Trimethylsilyl)prop-1-yneHCID 2724141Tetrabutylammonium FluorideHCID 38477704-Bromo-2-chloropyridine

Product 1

HCID 86667270HCID 86667270, compoundYield 67.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromo-2-chloropyridine (1.00 g, 5.20 mmol), 1-(trimethylsilyl)-1-propyne (0.846 mL, 5.72 mmol), copper(I) iodide (99 mg, 0.52 mmol), and tetrakis(triphenylphosphine)palladium(0) (90 mg, 0.08 mmol) were taken up in toluene (14 mL) in a microwave vial. Tetra-N-butylammonium fluoride (1M in THF) (6 mL, 6.00 mmol) was added and the reaction vessel was sealed and heated at 100° C. for 20 min in a microwave reactor. After cooling, the mixture was filtered through diatomaceous earth, and then concentrated in vacuo. The product was purified by flash chromatography using a gradient of EtOAc in heptane (0-50%) to give the title compound (530 mg, 67% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 2.11 (s, 3H), 7.38 (dd, 1H), 7.51 (s, 1H), 8.37 (d, 1H); MS (ES+) m/z 152 [M+H]+.

Workup

  1. customthe reaction vessel was sealed
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-5a304c52ef99489f91770ba74072cddf
Source dataset
uspto-grants-2016_02
Patent number
US09248129B2

Reaction notes

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