2-Bromoaniline → 5-(2-bromo-phenylcarbamoyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 83981

反応式

HRID 83981 の反応式
C[Al](C)C.[Br:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8].C[O:14][C:15]([C:17]1[CH2:18][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20][CH2:21][CH:22]=1)=O>ClCCl>[C:26]([O:25][C:23]([N:19]1[CH2:18][C:17]([C:15](=[O:14])[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[Br:5])=[CH:22][CH2:21][CH2:20]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

参加物

5

反応物 3

HCID 119922-BromoanilineHCID 111284441-Tert-butyl 3-methyl 1,2,5,6-tetrahydropyridine-1,3-dicarboxylateHCID 16682925Trimethylaluminum

生成物 1

HCID 689278695-(2-bromo-phenylcarbamoyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester収率 63.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Trimethylaluminium (2M in heptane, 3 ml) was added dropwise to a solution of 2-bromoaniline (860 mg) in dichloromethane (15 ml). After gas evolution ceased, 5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (Chem. Commun. 1999, 1757-1758, 1.2 g) dissolved in dichloromethane (10 ml) was added and the resulting mixture was refluxed for 5 hrs. The solution was cooled to 0° C., quenched by careful addition of saturated aqueous sodium bicarbonate (10 ml) and extracted with dichloromethane. The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 85:15) to afford 5-(2-bromo-phenylcarbamoyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.2 g), which was characterised by its mass and NMR spectra.

後処理

  1. additionwas added
  2. temperaturethe resulting mixture was refluxed for 5 hrs
  3. customquenched by careful addition of saturated aqueous sodium bicarbonate (10 ml)
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 85:15)

出典と根拠

ORDレコード
ord-ef6ef8d06845496a96b911312e08976f
出典データセット
uspto-grants-2014_09
特許番号
US08846907B2

関連ノート

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