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

HRID 632884Notes

Reaction equation

HRID 632884 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](N)=[N:6][CH:7]=1.[CH3:9][Si:10]([CH3:14])([CH3:13])[C:11]#[CH:12].[C:15]1(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>[CH3:15][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 706222-Amino-5-bromopyridine

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-pyridin-2-ylamine 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%).

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

Sources & evidence

ORD record
ord-908ecf9c412d4ba8bc618f969943c0c7
Source dataset
uspto-grants-2016_04
Patent number
US09321771B2

Reaction notes

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