Triethylamine → 5-Nitro-3-trimethylsilanylethynyl-pyridin-2-ylamine

HRID 563995Notes

Reaction equation

HRID 563995 reaction equation
[NH2:1][C:2]1[C:7](Br)=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14].C(N(CC)CC)C>O1CCCC1.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.[Cu]I>[N+:9]([C:5]1[CH:6]=[C:7]([C:17]#[C:16][Si:13]([CH3:15])([CH3:14])[CH3:12])[C:2]([NH2:1])=[N:3][CH:4]=1)([O-:11])=[O:10]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 27344122-Amino-3-bromo-5-nitropyridine

Product 1

HCID 115287895-Nitro-3-trimethylsilanylethynyl-pyridin-2-ylamine

Reagents, catalysts & solvents 3

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

Procedure

12.0 g 2-Amino-3-bromo-5-nitropyridine, 1.93 g dichlorobis(triphenyl-phosphine)palladium(II) and 0.524 g copper(I) iodide were dispersed under nitrogen in 60 ml dry tetrahydrofuran (THF). 7.03 g trimethylsilylacetylene and 16.71 g triethylamine were added and the mixture was stirred 16 hours (hrs) at room temperature (RT). The mixture was filtered, the filtrate was evaporated and the residue purified by chromatography on silica in ethyl acetate/heptane mixtures.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customthe residue purified by chromatography on silica in ethyl acetate/heptane mixtures

Sources & evidence

ORD record
ord-f0308c8edc3549229abe39b6071792ab
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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