Triethylamine → 6-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methyl-1H-quinolin-2-one

HRID 2112814Notes

Reaction equation

HRID 2112814 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[CH:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.I[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:34])[CH:28]=[C:27]2[CH3:35]>CN(C=O)C.[Cu]I>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[NH:30][C:29](=[O:34])[CH:28]=[C:27]4[CH3:35])=[N:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 126863636-Iodo-4-methylquinolin-2(1H)-oneHCID 578453285-(4-Chloro-phenyl)-2-ethynyl-pyridine

Product 1

HCID 690669966-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methyl-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

1.8 g (8.42 mmol) of 5-(4-chlorophenyl)-2-ethynylpyridine and 2.34 mL (16.84 mmol) of triethylamine are added to a suspension of 3.0 g (8.42 mmol) of 6-iodo-4-methyl-1H-quinolin-2-one in 20 mL of DMF and the mixture is evacuated three times and gassed with argon. Then 40.1 mg (0.21 mmol) of CuI and 153.9 mg (0.21 mmol) of PdCl2(dppf)-DCM complex are added and the mixture is evacuated again and gassed with argon. The reaction mixture is stirred overnight at RT, combined with EtOAc, and the precipitated product is filtered off and with washed EtOAc. The residue is stirred with a THF/water mixture (1:1), filtered, washed with THF, and dried in the circulating air dryer at 50° C. until the weight is constant. Yield: 3.10 g (99% of theoretical); C23H15ClN2O (M=370.831); calc.: molpeak (M+H)+: 371/373 (Cl); found: molpeak (M+H)+: 371/373 (Cl).

Workup

  1. customthe mixture is evacuated three times
  2. customthe mixture is evacuated again
  3. filtrationthe precipitated product is filtered off and with washed EtOAc
  4. stirringThe residue is stirred with a THF/water mixture (1:1)
  5. filtrationfiltered
  6. washwashed with THF
  7. customdried in the circulating air dryer at 50° C. until the weight

Sources & evidence

ORD record
ord-28e89a6d321640f68a33f7073f3946f0
Source dataset
uspto-grants-2009_04
Patent number
US07524862B2

Reaction notes

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