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Propargyl bromide → 6,6-Dimethyl-8-morpholin-4-yl-9-(3-morpholin-4-yl-prop-1-ynyl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61791
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HRID 61791 반응식
Br[C:2]1[C:23]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:22][C:5]2[C:6]([CH3:21])([CH3:20])[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[C:16](=[O:17])[C:4]=2[CH:3]=1)=[CH:13][CH:12]=[C:11]([C:18]#[N:19])[CH:10]=4.Br[CH2:31][C:32]#[CH:33].[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[Cs+].[Cs+]>O.C(#N)C>[CH3:20][C:6]1([CH3:21])[C:7]2[NH:8][C:9]3[C:14](=[CH:13][CH:12]=[C:11]([C:18]#[N:19])[CH:10]=3)[C:15]=2[C:16](=[O:17])[C:4]2[CH:3]=[C:2]([C:33]#[C:32][CH2:31][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:23]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:22][C:5]1=2
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참가 물질

8

반응물 5

HCID 7842Propargyl bromideHCID 8083MorpholineHCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 66834380HCID 66834380, 화합물

생성물 1

HCID 668343076,6-Dimethyl-8-morpholin-4-yl-9-(3-morpholin-4-yl-prop-1-ynyl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

To 9-bromo-6,6-dimethyl-8-morpholin-4-yl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound F3-4, 30 mg, 0.067 mmol), 3-bromopropyne (0.01 ml, 0.13 mmol), morpholine (0.029 ml, 0.33 mmol), X-Phos (4.8 mg, 15% mol), PdCl2 (CH3CN)2 (0.9 mg, 5% mol) and cesium carbonate (87 mg, 0.27 mmol), acetonitrile (2 ml) was added and the mixture was stirred at 80° C. for 2 hr. The reaction solution was added to water, and then extracted with dichloromethane. The organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (dichloromethane/methanol) to obtain the target compound (pale brown solid, 18 mg, 64%).

후처리

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customThe drying agent was removed by filtration
  4. customthe residues obtained
  5. concentrationafter concentration under reduced pressure
  6. customwere purified by silica gel column chromatography (dichloromethane/methanol)
  7. customto obtain the target compound (pale brown solid, 18 mg, 64%)

출처 및 근거

ORD 기록
ord-58fa4f8cf73948a8a690fd63a6c1f86d
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09440922B2

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