Hydrochloric Acid → 8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-4,6,6-trimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2275228ノート

反応式

HRID 2275228 の反応式
Br[C:2]1[C:3]([C:31]#[N:32])=[CH:4][CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[C:11]([CH3:16])([CH3:15])[C:10]3[CH:17]=[C:18]([O:21][CH2:22][C@H:23]4[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]4)[CH:19]=[CH:20][C:9]=3[C:8](=[O:30])[C:7]2=1.[Cl-].[Li+].[CH3:35][Sn](C)(C)C.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.Cl>CN(C=O)C>[CH3:29][C:25]1([CH3:28])[O:24][C@@H:23]([CH2:22][O:21][C:18]2[CH:19]=[CH:20][C:9]3[C:8](=[O:30])[C:7]4[C:6]5[C:14](=[C:2]([CH3:35])[C:3]([C:31]#[N:32])=[CH:4][CH:5]=5)[NH:13][C:12]=4[C:11]([CH3:16])([CH3:15])[C:10]=3[CH:17]=2)[CH2:27][O:26]1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 11661TetramethyltinHCID 75806TricyclohexylphosphineHCID 433294Lithium ChlorideHCID 668348924-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

生成物 1

HCID 668348858-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-4,6,6-trimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

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, 4-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound U8-1, 30.0 mg, 60.56 μmol) and lithium chloride (7.70 mg, 181.7 μmol) were dissolved in DMF (1.00 mL), added with tetramethyl tin (12.5 μL, 90.84 μmol), tetrakistriphenylphosphine palladium (3.50 mg, 6.056 μmol) and tricyclohexylphosphine (toluene solution, 20 wt %, 17.0 mg, 3.028 μmol), and the mixture was stirred at 100° C. for 24 hr. The reaction solution was poured into hydrochloric acid (1 M), extracted with ethyl acetate, washed with water, saturated aqueous solution of sodium bicarbonate and saturated brine, dried over sodium sulfate, and then filtered. The residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain 8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-4,6,6-trimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile as a crude product (20.9 mg, 80%).

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with water, saturated aqueous solution of sodium bicarbonate and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-94a8e05f9e1f4fee870e29c6d621be06
出典データセット
uspto-grants-2015_09
特許番号
US09126931B2

反応ノート

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