m-Anisoyl chloride → 3-methoxy-N-methyl-N-(4-(pyridin-2-yl)but-3-ynyl)benzamide

HRID 1189278Notes

Reaction equation

HRID 1189278 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.CCN(C(C)C)C(C)C.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28]>C(Cl)Cl>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([N:2]([CH3:1])[CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:28]

Participants

5

Reactant 3

HCID 74374m-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 66598286N-methyl-4-(pyridin-2-yl)but-3-yn-1-amine

Product 1

HCID 665982693-methoxy-N-methyl-N-(4-(pyridin-2-yl)but-3-ynyl)benzamideYield 63.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Methyl-4-(pyridin-2-yl)but-3-yn-1-amine (50 mg, 0.31 mmol) was dissolved in DCM (2 mL) and DIEA (67 μl, 0.41 mmol) was added at room temperature. The resulting mixture was cooled to 0° C. before the addition of 3-methoxybenzoyl chloride (69 mg, 0.41 mmol). After stirring overnight at room temperature, the mixture was quenched with water and extracted with DCM. DCM fractions were washed with water (10 mL), NaHCO3 sat (2*10 mL), water (10 mL), brine (10 mL). The solvent was removed and the crude residue was purified over silicagel chromatography (prepacked 10 g silicagel column, DCM/MeOH: from 100/0 to 95/5 as eluent) to afford 58 mg of 3-methoxy-N-methyl-N-(4-(pyridin-2-yl)but-3-ynyl)benzamide (Yield: 63%) as a brown oil.

Workup

  1. customthe mixture was quenched with water
  2. extractionextracted with DCM
  3. washDCM fractions were washed with water (10 mL), NaHCO3
  4. customThe solvent was removed
  5. customthe crude residue was purified over silicagel chromatography (prepacked 10 g silicagel column, DCM/MeOH: from 100/0 to 95/5 as eluent)

Sources & evidence

ORD record
ord-64e7487d2a7f44019e35629ae65d1995
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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