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

HRID 2112814ノート

反応式

HRID 2112814 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-28e89a6d321640f68a33f7073f3946f0
出典データセット
uspto-grants-2009_04
特許番号
US07524862B2

反応ノート

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