Cesium carbonate → 8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-9-[(triisopropylsilanyl)-ethynyl]-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61792

反応式

HRID 61792 の反応式
Br[C:2]1[C:23]([N:24]2[CH2:29][CH2:28][N:27]([CH:30]3[CH2:33][CH2:32][CH2:31]3)[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.[C:34]([Si:36]([CH:43]([CH3:45])[CH3:44])([CH:40]([CH3:42])[CH3:41])[CH:37]([CH3:39])[CH3:38])#[CH:35].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N>[CH:30]1([N:27]2[CH2:26][CH2:25][N:24]([C:23]3[C:2]([C:35]#[C:34][Si:36]([CH:37]([CH3:39])[CH3:38])([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41])=[CH:3][C:4]4[C:16](=[O:17])[C:15]5[C:14]6[C:9](=[CH:10][C:11]([C:18]#[N:19])=[CH:12][CH:13]=6)[NH:8][C:7]=5[C:6]([CH3:21])([CH3:20])[C:5]=4[CH:22]=3)[CH2:29][CH2:28]2)[CH2:33][CH2:32][CH2:31]1

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 2734682(Triisopropylsilyl)acetyleneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 498048699-bromo-8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

生成物 1

HCID 668344028-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-9-[(triisopropylsilanyl)-ethynyl]-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile収率 74.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Under nitrogen atmosphere, to the MeCN (8 ml) suspension of 9-bromo-8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound F4-10, 200 mg, 0.397 mmol), ethynyltriisopropylsilane (268 mg, 3.0 eq.), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (Xphos) (39 mg, 0.2 eq.), Pd(CH3CN)2Cl2 (11 mg, 0.1 eq.) and cesium carbonate (518 mg, 4.0 eq.) were added and the mixture was stirred and heated under reflux condition until the reaction is completed. Upon the completion of the reaction, distilled water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with brine and 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 (ethyl acetate/methanol) to obtain 8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-9-[(triisopropylsilanyl)-ethynyl]-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (179 mg, 74%).

後処理

  1. additionwere added
  2. temperatureheated
  3. temperatureunder reflux condition until the reaction
  4. customUpon the completion of the reaction
  5. distillationdistilled water
  6. additionwas added to the reaction solution, which
  7. extractionwas then extracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over sodium sulfate
  10. customThe drying agent was removed by filtration
  11. customthe residues obtained
  12. concentrationafter concentration under reduced pressure
  13. customwere purified by silica gel column chromatography (ethyl acetate/methanol)

出典と根拠

ORDレコード
ord-d791f9348c1f46d9af1498e06702e1a0
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

関連ノート

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