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Dimethylformamide → tert-Butyl 7-cyano-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 242108
ノート
印刷プレビュー

反応式

HRID 242108 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18](OS(C(F)(F)F)(=O)=O)[CH:19]=3)[CH2:14][CH2:13][N:12]2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:10][CH2:9][CH2:8]1.[CH3:36][N:37](C)C=O>C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].[C-]#N.[Zn+2].[C-]#N>[C:36]([C:18]1[CH:19]=[C:20]2[C:15]([CH2:14][CH2:13][N:12]([C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[CH:11]2[C:7]2([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:10][CH2:9][CH2:8]2)=[CH:16][CH:17]=1)#[N:37]
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

5

反応物 2

HCID 6228DimethylformamideHCID 58246194tert-Butyl 1-[1-(pyridin-2-yl)cyclobutyl]-7-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydroisoquinoline-2(1H)-carboxylate

生成物 1

HCID 58246239tert-Butyl 7-cyano-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒
HCID 15826098
Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+)
触媒

反応条件

温度
90 °C

実験手順

Dipalladium trisdibenzylidene acetone (0.14 g, 0.153 mmol) and diphenylphosphinoferrocene (0.338 g, 0.61 mmol) were suspended in dimethylformamide (15 ml) under an argon atmosphere. tert-Butyl 1-[1-(pyridin-2-yl)cyclobutyl]-7-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.782 g, 1.562 mmol) was added and the reaction mixture was heated to 90° C. Zinc cyanide (0.215 g, 1.831 mmol) was added over 30 min in small portions. Stirring at 90° C. was continued for 15 min. After cooling to room temperature the catalyst was removed by filtration and washed with dimethylformamide. The dimethylformamide filtrate was poured in water (200 ml). The water was extracted with dichloromethane (3×). The combined organic extracts were washed with water, dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane, methanol). Yield: 197 mg (0.506 mmol, 33%).

後処理

  1. temperatureAfter cooling to room temperature the catalyst
  2. customwas removed by filtration
  3. washwashed with dimethylformamide
  4. additionThe dimethylformamide filtrate was poured in water (200 ml)
  5. extractionThe water was extracted with dichloromethane (3×)
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography (silica, dichloromethane, methanol)

出典と根拠

ORDレコード
ord-4d3258f937c347e395c5fd2d4b189554
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08653100B2

反応ノート

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