Triethylamine → 5-Chloro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

HRID 402595

Reaction equation

HRID 402595 reaction equation
[NH2:1][C:2]1[C:7](I)=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[C:17]([Si:19]([CH3:22])([CH3:21])[CH3:20])#[CH:18]>O1CCCC1.C(OCC)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>[NH2:1][C:2]1[C:7]([C:18]#[C:17][Si:19]([CH3:22])([CH3:21])[CH3:20])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 110760102-Amino-5-chloro-3-iodopyridine

Product 1

HCID 247294655-Chloro-3-((trimethylsilyl)ethynyl)pyridin-2-amineYield 109.9%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 2-amino-5-chloro-3-iodopyridine (4.2 g, 0.017 mol), copper(I) iodide (0.032 g, 0.17 mmol) and triethylamine (7.0 mL, 0.050 mol) in anhydrous tetrahydrofuran (10 mL), dichlorobis(triphenylphosphine)palladium(II) (0.12 g, 0.17 mmol) and ethynyl trimethylsilane (3.0 mL, 0.021 mol) were added and the mixture was stirred at ambient temperature for 2 h. The reaction mixture was diluted with diethyl ether and removed the precipitate by filtration with C elite. The filtrate was concentrated to afford 2-amino-5-chloro-3-[(trimethylsilyl)ethynyl]pyridine as solid (4.2 g).

Workup

  1. customremoved the precipitate
  2. filtrationby filtration with C elite
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-84fa41631148433bab00c109d60ee98d
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Linked notes

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