Trimethylsilylacetylene → 3-(Pyrrolidin-1-ylmethyl)-5-[(trimethylsilyl)ethynyl]pyridine

HRID 1255916Notes

Reaction equation

HRID 1255916 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:7]=1.[C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])#[CH:15].C(N(C(C)C)CC)(C)C>CN(C=O)C.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.[Cu]I>[N:9]1([CH2:8][C:6]2[CH:5]=[N:4][CH:3]=[C:2]([C:15]#[C:14][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:7]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

7

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 212559453-Bromo-5-(pyrrolidin-1-ylmethyl)pyridine

Product 1

HCID 212559323-(Pyrrolidin-1-ylmethyl)-5-[(trimethylsilyl)ethynyl]pyridine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-bromo-5-(pyrrolidin-1-ylmethyl)pyridine (0.76 mmol), ethynyltrimethylsilane (0.91 mmol), Pd(PPh3)4 (0.038 mmol), CuI (0.076 mmol), and 0.26 mL (1.52 mmol) of diisopropylethylamine in 3.8 mL of DMF can be heated at 50° C. overnight under an atmosphere of N2. Upon cooling to ambient temperature, the reaction mixture is concentrated and the crude product is purified by silica gel flash chromatography (eluted with 50% EtOAc/hexanes).

Workup

  1. temperatureUpon cooling to ambient temperature
  2. concentrationthe reaction mixture is concentrated
  3. customthe crude product is purified by silica gel flash chromatography (eluted with 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1c399858d05c49b3bda92158e3a477b2
Source dataset
uspto-grants-2013_06
Patent number
US08461167B2

Reaction notes

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