m-Xylyl bromide → 3-(3-Methyl-benzoyl)-1-(3-methyl-benzyl)-1H-quinolin-4-one

HRID 226947

反応式

HRID 226947 の反応式
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[C:7]([CH:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH2:10]1)=[O:8].[CH3:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Br>CN(C)C=O>[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[C:7]([C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:23][C:24]2[CH:31]=[CH:30][CH:29]=[C:26]([CH3:27])[CH:25]=2)[CH:10]=1)=[O:8]

参加物

5

反応物 3

HCID 12099m-Xylyl bromideHCID 24758Sodium hydrideHCID 670719523-(3-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one

生成物 1

HCID 167308533-(3-Methyl-benzoyl)-1-(3-methyl-benzyl)-1H-quinolin-4-one収率 50.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Compound 4y was prepared following the procedure outlined in Step 3 of Example 1 using 26 mg (0.65 mmol) of sodium hydride (60%), 132 mg (0.50 mmol) of 3-(3-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one, 3 mL of anhydrous dimethylformamide, and 120 mg (0.65 mmol) of 3-methylbenzylbromide. The crude product was purified by flash chromatography to yield 92 mg of a colorless solid 4y: LC-MSD, m/z for C25H21NO2, [M+H]+=368.5, [M+2H]+=369.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.586 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.37 (s, 3H), 2.42 (s, 3H), 5.39 (s, 2H), 7.01 (d, 2H), 7.15 (d, 1H), 7.22-7.44 (m, 5H), 7.55-7.58 (m, 3H), 8.29 (s, 1H), 8.47 (d, 1H).

後処理

  1. customCompound 4y was prepared
  2. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-90fef07af96448c2948cb4a7c9a94fe4
出典データセット
uspto-grants-2009_07
特許番号
US07557213B2

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