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Propargyl bromide → 1-(propa-1,2-dienyl)-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride

HRID 1932358
ノート
印刷プレビュー

反応式

HRID 1932358 の反応式
[H-].[Na+].[CH2:3](Br)[C:4]#[CH:5].[ClH:7].[CH2:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:18]1[N:19]=[CH:20][CH:21]=[C:22]2[C:26]([CH3:27])=[C:25]([CH3:28])[NH:24][C:23]=12>O1CCCC1>[ClH:7].[CH:3]([N:24]1[C:23]2=[C:18]([N:9]3[CH2:10][CH2:11][C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:8]3)[N:19]=[CH:20][CH:21]=[C:22]2[C:26]([CH3:27])=[C:25]1[CH3:28])=[C:4]=[CH2:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 671411697-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride

生成物 1

HCID 866152531-(propa-1,2-dienyl)-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride収率 6.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

実験手順

Sodium hydride (60%; 80 mg, 1.80 mmol) and propargyl bromide (35.6 μl, 1.40 mmol) were added at 0° C. to a solution of 7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride (92.3 mg, 0.33 mol) prepared in Example 468 in anhydrous tetrahydrofuran (10 ml). The reaction mixture was stirred for 12 hours at room temperature. Ice was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate=1/1, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 32.5 mg of the titled compound as a white solid.

後処理

  1. additionIce was added to the reaction mixture, which
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate=1/1
  6. dissolutionThe resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-a8d76ce6abc24936befbdc98b495437a
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08188114B2

反応ノート

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