N-methyl-2-pyrrolidone → HCID 131729277, compound

HRID 557256Notes

Reaction equation

HRID 557256 reaction equation
I[C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:9][Si:10](C#C)([CH3:12])[CH3:11].[CH:15](N(CC)C(C)C)(C)[CH3:16].CN1CCCC1=O>[Cu]I.[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.O>[CH3:9][Si:10]([CH3:12])([CH3:11])[C:2]1[C:3]([NH:8][C:15]#[CH:16])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 27631512-Amino-3-iodopyridine

Product 1

HCID 131729277HCID 131729277, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

To a mixture of 3-iodo-pyridin-2-ylamine described in Preparation Example 1-1-3 (40.2 g, 183 mmol), trimethylsilyl acetylene (51.7 mL, 366 mmol), copper(I) iodide (3.49 g, 18.3 mmoL), N,N-diisopropyl ethyl amine (63.7 mL, 366 mmol), N-methylpyrrolidinone (200 mL) was added tetrakis(triphenyl phosphine) palladium (0) (10.6 g, 9.15 mmol), which was stirred at room temperature for 3 hours 10 minutes under a nitrogen stream. To the reaction solution was added water and extracted four times with ethyl acetate. The solvent thereof was concentrated under a reduced pressure. The residue was purified by NH silica gel chromatography (heptane:ethyl acetate=4:1). The resulting solution was concentrated under a reduced pressure and the residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1 then 1:1) to obtain the title compound (28.1 g).

Workup

  1. extractionextracted four times with ethyl acetate
  2. concentrationThe solvent thereof was concentrated under a reduced pressure
  3. customThe residue was purified by NH silica gel chromatography (heptane:ethyl acetate=4:1)
  4. concentrationThe resulting solution was concentrated under a reduced pressure
  5. customthe residue was purified by silica gel chromatography (heptane

Sources & evidence

ORD record
ord-b26c6ec978b342c0a2020066a95e03ba
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

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