Sodium hydride → 3-(3-Methyl-benzoyl)-1-pyridin-2-ylmethyl-1H-quinolin-4-one

HRID 226945

反応式

HRID 226945 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].Br.Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1>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]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH:10]=1)=[O:8]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 670719523-(3-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one

生成物 1

HCID 167308553-(3-Methyl-benzoyl)-1-pyridin-2-ylmethyl-1H-quinolin-4-one収率 31%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Compound 4w was prepared following the procedure outlined in Step 3 of Example 1 using 52 mg (1.3 mmol) of sodium hydride (60%), 132 mg (0.5 mmol) of 3-(3-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3g, 3 mL of anhydrous dimethylformamide, and 164 mg (0.65 mmol) of 2-bromomethylpyridine hydrobromide. The crude product was purified by flash chromatography to yield 55 mg of a pale yellow solid 4w: Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=1.913 min; LC-MSD, m/z for C23H18N2O2, [M+H]+=355.4, [M+2H]+=356.4; 1H NMR (400 MHz, CDCl3/HCl): δ 2.40 (s, 3H), 5.50 (s, 2H), 7.12 (d, 1H), 7.22-7.35 (m, 3H), 7.38-7.46 (m, 2H), 7.56-7.68 (m, 4H), 8.56 (s, 1H), 8.46 (d, 1H), 8.62 (d, 1H).

後処理

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

出典と根拠

ORDレコード
ord-d7af22b2efb1433daf8f591c03251df2
出典データセット
uspto-grants-2009_07
特許番号
US07557213B2

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