tert-Butyl piperazine-1-carboxylate → HCID 69196293, 화합물

HRID 2116517노트

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HRID 2116517 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 69196293HCID 69196293, 화합물수율 39%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
150 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c960b2a8cf534f5b981f39e8a5e8d3a3
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07439243B2

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