Triethylamine → 2-Methyl-5-((trimethylsilyl)ethynyl)pyridine

HRID 1529195Notes

Reaction equation

HRID 1529195 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.[CH3:9][Si:10]([CH3:14])([CH3:13])[C:11]#[CH:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=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>[CH3:8][C:5]1[CH:4]=[CH:3][C:2]([C:12]#[C:11][Si:10]([CH3:14])([CH3:13])[CH3:9])=[CH:7][N:6]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 12010205-Bromo-2-methylpyridine

Product 1

HCID 155537632-Methyl-5-((trimethylsilyl)ethynyl)pyridine

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound is synthesized according to general procedure GP2 starting from 2.0 g (11.6 mmol) 5-bromo-2-methyl-pyridine and 2.3 mL (16.3 mmol) 1-trimethylsilyl-ethyne using 68 mg (0.36 mmol) CuI, 305 mg (1.2 mmol) triphenylphosphine, 213 mg (0.30 mmol) PdCl2(PPh3)2 and 18 mL (127 mmol) triethylamine in 18 mL dry THF. For the work-up the reaction mixture is diluted with ethyl acetate, the organic phase is extracted with water and brine. The product is purified by chromatography on silica gel using a hexane/ethyl acetate gradient. Yield: 1.5 g (68%). Note: Sublimation of the product is observed at 40° C./40 mbar.

Workup

  1. extractionthe organic phase is extracted with water and brine
  2. customThe product is purified by chromatography on silica gel using a hexane/ethyl acetate gradient
  3. customis observed at 40° C.

Sources & evidence

ORD record
ord-a1987f00097744868869c68f326e3b2c
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

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