Potassium Carbonate → 8-(4-Cyclobutyl-piperazin-1-yl)-6,6,9-trimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2275169

反応式

HRID 2275169 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.[CH3:34]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:30]1([N:27]2[CH2:26][CH2:25][N:24]([C:23]3[C:2]([CH3:34])=[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

5

反応物 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 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 668347598-(4-Cyclobutyl-piperazin-1-yl)-6,6,9-trimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile収率 59.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Under nitrogen atmosphere, to the N,N-dimethyl formamide (1.5 ml) solution 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, 50 mg, 0.099 mmol), trimethyl boroxine (12 mg, 0.1 eq.), tetrakis triphenylphosphine palladium (39 mg, 0.2 eq.), and potassium carbonate (41 mg, 3.0 eq.) were added, and the mixture was stirred at 100° C. for 24 hr. 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 the title compound (25 mg, 58%).

後処理

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

出典と根拠

ORDレコード
ord-475e25c7cc1f47468a41d1184080954f
出典データセット
uspto-grants-2015_09
特許番号
US09126931B2

関連ノート

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