Water → HCID 131729277, compound

HRID 557258Notes

Reaction equation

HRID 557258 reaction equation
[NH2:1][C:2]1[C:7](Br)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][Si:10](C#C)([CH3:12])[CH3:11].[CH:15](N(CC)C(C)C)(C)[CH3:16].O>CN1CCCC1=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[CH3:9][Si:10]([CH3:12])([CH3:11])[C:7]1[C:2]([NH:1][C:15]#[CH:16])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 8177002-Amino-3-bromopyridine

Product 1

HCID 131729277HCID 131729277, compoundYield 94.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-amino-3-bromopyridine (5.72 g, 33.1 mmol) in N-methylpyrrolidinone (120 mL) were added trimethylsilyl acetylene (9.36 mL, 66.2 mmol), tetrakis(triphenyl phosphine) palladium (0) (1.91 g, 1.66 mmol), copper (I) iodide (630 mg, 3.31 mmol) and N,N-diisopropyl ethyl amine (11.5 mL, 66.2 mmol) at room temperature, which was stirred at 70° C for 6 hours under a nitrogen atmosphere. To the reaction solution was added water, and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride water, dried over anhydrous magnesium sulfate, and the solvent thereof was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (5.94 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated sodium chloride water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent thereof was evaporated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-8234492ea94a49018b62a0b502a19dff
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

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