Triethylamine → 6-Ethyl-5-trimethylsilanylethynyl-pyridin-2-ylamine

HRID 1916176Notes

Reaction equation

HRID 1916176 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1I)[CH3:2].[CH3:11][Si:12]([CH3:16])([CH3:15])[C:13]#[CH:14].C(N(CC)CC)C>C1COCC1.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>[CH2:1]([C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:14]#[C:13][Si:12]([CH3:16])([CH3:15])[CH3:11])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 216639766-Ethyl-5-iodopyridin-2-amine

Product 1

HCID 580729006-Ethyl-5-trimethylsilanylethynyl-pyridin-2-ylamine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound is synthesized according to general procedure GP2 starting from 18 g (72.6 mmol) 6-ethyl-5-iodo-pyridin-2-ylamine and 14.4 mL (102 mmol) 1-trimethylsilyl-ethyne using 1.38 g (7.3 mmol) CuI, 5.1 g (7.3 mmol) PdCl2(PPh3)2 and 101 mL (726 mmol) triethylamine in 100 mL dry THF. For the work-up the solvent is removed under reduced pressure, the crude product is taken up in ethyl acetate and the organic phase is extracted with water. The product is purified twice by chromatography on silica gel using a cyclohexane/ethyl acetate gradient. Yield: 12.73 g (80%).

Workup

  1. customFor the work-up the solvent is removed under reduced pressure
  2. extractionthe organic phase is extracted with water
  3. customThe product is purified twice by chromatography on silica gel using a cyclohexane/ethyl acetate gradient

Sources & evidence

ORD record
ord-59cfe14a172f49ba916c56841a3d1815
Source dataset
uspto-grants-2013_12
Patent number
US08618111B2

Reaction notes

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