3-(Methoxycarbonyl)benzeneboronic acid → Methyl 3-{2-methyl-3-[(2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)-carbonyl]indolizin-1-yl}benzoate

HRID 535457ノート

反応式

HRID 535457 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)=[O:4].O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:25]1[C:26]([CH3:48])=[C:27]([C:34]([C:36]2[CH:37]=[C:38]3[C:43](=[CH:44][CH:45]=2)[N:42]=[C:41]([CH3:46])[NH:40][C:39]3=[O:47])=[O:35])[N:28]2[C:33]=1[CH:32]=[CH:31][CH:30]=[CH:29]2>O.CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:48][C:26]1[C:25]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[O:4])=[C:33]2[N:28]([C:27]=1[C:34]([C:36]1[CH:37]=[C:38]3[C:43](=[CH:44][CH:45]=1)[N:42]=[C:41]([CH3:46])[NH:40][C:39]3=[O:47])=[O:35])[CH:29]=[CH:30][CH:31]=[CH:32]2

参加物

7

反応物 3

HCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 23436936Potassium phosphate dihydrateHCID 1363654746-[(1-bromo-2-methylindolizin-3-yl)carbonyl]-2-methylquinazolin-4(3H)-one

生成物 1

HCID 136365475Methyl 3-{2-methyl-3-[(2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)-carbonyl]indolizin-1-yl}benzoate収率 58.6%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

0.139 g (0.78 mmol) of [3-(methoxycarbonyl)phenyl]boronic acid, 0.321 g (1.29 mmol) of potassium phosphate dihydrate dissolved in 0.81 ml of water, and 0.0149 g (0.01 mmol) of tetrakis(triphenylphosphine)palladium are added, under an argon atmosphere at ambient temperature, to 0.256 g (0.65 mmol) of 6-[(1-bromo-2-methylindolizin-3-yl)carbonyl]-2-methylquinazolin-4(3H)-one in 9 ml of DMF. The reaction medium is microwave-heated at 150° C. for 15 minutes. After dilution with ethyl acetate, the organic phase is washed with a 1N aqueous solution of hydrochloric acid and then a saturated aqueous solution of sodium chloride, dried over sodium sulphate, filtered, and then concentrated under reduced pressure. The solid obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (95/2) mixture. 172 mg of a yellow solid are obtained.

後処理

  1. washAfter dilution with ethyl acetate, the organic phase is washed with a 1N aqueous solution of hydrochloric acid
  2. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe solid obtained
  6. customis purified by silica gel column chromatography, elution

出典と根拠

ORDレコード
ord-9fa617bd4b40479ab9e65213502979b4
出典データセット
uspto-grants-2014_10
特許番号
US08859544B2

反応ノート

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