Triethylamine → 5-Nitro-3-(phenylethynyl)pyridin-2-amine

HRID 1435585Notes

Reaction equation

HRID 1435585 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.C(N(CC)CC)C.[C:19]1([C:25]#[CH:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1.[Cu]I>[N+:9]([C:5]1[CH:6]=[C:7]([C:26]#[C:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:2]([NH2:1])=[N:3][CH:4]=1)([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 27344122-Amino-3-bromo-5-nitropyridine

Product 1

HCID 593229015-Nitro-3-(phenylethynyl)pyridin-2-amine

Reagents, catalysts & solvents 2

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

Procedure

1.83 g 2-amino-3-bromo-5-nitropyridine 0.29 g PdCl2(PPh3)2 and 79 mg CuI were mixed in 36 ml dry tetrahydrofuran (THF) and 3.45 ml triethylamine and 1.12 g phenylacetylene were added. Stirring was continued at room temperature for 12 hrs, then the solvent was removed and the residue purified by flash chromatography on silica in ethyl acetate/heptane eluent. Yield 855 mg.

Workup

  1. customthe solvent was removed
  2. customthe residue purified by flash chromatography on silica in ethyl acetate/heptane eluent

Sources & evidence

ORD record
ord-4d14ad169c804737b6cec9725c20d544
Source dataset
uspto-grants-2009_11
Patent number
US07618964B2

Reaction notes

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