tert-Butyl piperazine-1-carboxylate → HCID 69196293、化合物

HRID 2116517ノート

反応式

HRID 2116517 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3Cl)=[O:9])[CH:5]=[CH:6][CH:7]=1.[N:21]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[N:24]2[CH2:23][CH2:22][N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25]2)=[O:9])[CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 69195748HCID 69195748、化合物

生成物 1

HCID 69196293HCID 69196293、化合物収率 39%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
150 °C

実験手順

A stirred suspension of (3-chlorophenyl)(8-chloro-3-quinolinyl)methanone (D5)(0.63 g, 2.1 mmol), 1,1-dimethylethyl 1-piperazinecarboxylate (0.43 g, 2.3 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.058 g, 0.064 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.074 g, 0.19 mmol) and sodium tert-butoxide (0.22 g, 2.3 mmol) in degassed toluene (3.5 ml) was heated in a sealed tube at 150° C. for 10 mins in a microwave oven. The cooled reaction mixture was washed with water (20 ml), dried (MgSO4) and concentrated in vacuo to an oil. The oil was purified by chromatography over silica gel eluting with a gradient of ethyl acetate/hexane to afford the title compound (D6) as a yellow foam (0.37 g, 0.81 mmol, 39%).

後処理

  1. customThe cooled reaction mixture
  2. washwas washed with water (20 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo to an oil
  5. customThe oil was purified by chromatography over silica gel eluting with a gradient of ethyl acetate/hexane

出典と根拠

ORDレコード
ord-c960b2a8cf534f5b981f39e8a5e8d3a3
出典データセット
uspto-grants-2008_10
特許番号
US07439243B2

反応ノート

読み込み中…