Cesium carbonate → tert-Butyl 3-(2-methoxy-2-oxo-ethyl)-4-(2-methyl-4-quinolyl)piperazine-1-carboxylate

HRID 333981

반응식

HRID 333981 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.[CH3:13][O:14][C:15](=[O:30])[CH2:16][CH:17]1[NH:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=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].C1(C)C=CC=CC=1>[CH3:13][O:14][C:15](=[O:30])[CH2:16][CH:17]1[N:22]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:12])[CH:3]=2)[CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:18]1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 779734-Chloro-2-methylquinolineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)2회HCID 2756816Methyl 4-Boc-piperazine-2-acetate

생성물 1

HCID 86691601tert-Butyl 3-(2-methoxy-2-oxo-ethyl)-4-(2-methyl-4-quinolyl)piperazine-1-carboxylate수율 17.4%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매2회HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

4-Chloroquinaldine (263 mg, 1.481 mmol), tert-butyl 3-(2-methoxy-2-oxo-ethyl)piperazine-1-carboxylate (318 mg, 1.231 mmol) and caesium carbonate (885 mg, 2.72 mmol) were mixed with anhydrous toluene (4 ml) in an argon atmosphere. 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (128 mg, 0.221 mmol) and tris(dibenzylideneacetone)dipalladium(0) (67 mg, 0.073 mmol) were added and the resulting mixture was stirred at 110° C. for six hours. Additional 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (128 mg, 0.221 mmol) and tris(dibenzylideneacetone)dipalladium(0) (67 mg, 0.073 mmol) were added and the mixture was stirred at 110° C. overnight. After reaching room temperature the mixture was filtered, the filtrate was evaporated to dryness to give a red oil that was purified by column chromatography (silica, gradient from DCM to DCM/methanol 1:20) to yield 136 mg of a yellow foam (0.214 mmol, 17%). MS (ESI) m/z=400.2 [M+1]+.

후처리

  1. stirringthe mixture was stirred at 110° C. overnight
  2. customAfter reaching room temperature
  3. filtrationwas filtered
  4. customthe filtrate was evaporated to dryness
  5. customto give a red oil that
  6. customwas purified by column chromatography (silica, gradient from DCM to DCM/methanol 1:20)

출처 및 근거

ORD 기록
ord-80add02432bd4de7aa17912980a74a87
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883791B2

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