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1-Propanol → 6,6-Dimethyl-11-oxo-8-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61754
ノート
印刷プレビュー

反応式

HRID 61754 の反応式
[C:1]([C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:8](=[O:30])[C:9]4[CH:21]=[CH:20][C:19](OS(C(F)(F)F)(=O)=O)=[CH:18][C:10]=4[C:11]([CH3:17])([CH3:16])[C:12]=3[NH:13]2)=[CH:5][CH:4]=1)#[N:2].[CH2:31](O)[CH2:32]C.C([B-](F)(F)F)=C.[K+].C(N(CC)CC)C>O>[CH3:16][C:11]1([CH3:17])[C:12]2[NH:13][C:14]3[C:6](=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[CH:15]=3)[C:7]=2[C:8](=[O:30])[C:9]2[CH:21]=[CH:20][C:19]([CH:31]=[CH2:32])=[CH:18][C:10]1=2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 10311-PropanolHCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 86663817Trifluoro-methanesulfonic acid 3-cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yl ester2 回

生成物 1

HCID 668340546,6-Dimethyl-11-oxo-8-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile収率 80%

試薬・触媒・溶媒

1
HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

Under nitrogen atmosphere, trifluoro-methanesulfonic acid 3-cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yl ester (Compound B1, 1.00 g, 2.302 mmol) was added with n-propanol (20 mL), potassium vinyltrifluoroborate (854 mg, 3.0 eq.), dichloro-((bis-diphenylphosphino)ferrocenyl)palladium (217 mg, 0.1 eq.) and triethylamine (1.11 ml, 3.0 eq.) in order and the resultant was stirred at 60° C. for 4 hr. Upon the completion of the reaction, water was added to the reaction solution. The resulting precipitates were filtered and washed with distilled water, and the residues were dried to obtain the title compound (666 mg, 80%).

後処理

  1. additionwas added to the reaction solution
  2. customThe resulting precipitates
  3. filtrationwere filtered
  4. washwashed with distilled water
  5. customthe residues were dried

出典と根拠

ORDレコード
ord-27637dfe19f8455bb26f5e4928000c58
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09440922B2

反応ノート

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