Ammonium Chloride → 7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride

HRID 1445069ノート

反応式

HRID 1445069 の反応式
[CH3:1][C:2]([Mg]Br)=[CH:3][CH3:4].[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][N:8]1[C:17]1[C:22]([N+:23]([O-])=O)=[CH:21][CH:20]=[CH:19][N:18]=1.[Cl-:26].[NH4+]>O1CCCC1>[ClH:26].[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][N:8]1[C:17]1[N:18]=[CH:19][CH:20]=[C:21]2[C:3]([CH3:4])=[C:2]([CH3:1])[NH:23][C:22]=12

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 9196247Isoquinoline, 1,2,3,4-tetrahydro-2-(3-nitro-2-pyridinyl)-HCID 178448414HCID 178448414、化合物

生成物 1

HCID 671411697-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution; 112 ml) was slowly added at −78° C. to a solution of 2-(1,2,3,4-tetrahydroisoquinolin-2-yl)-3-nitropyridine (4.8 g, 18.8 mmol) prepared in Preparation 20 in anhydrous tetrahydrofuran (150 ml). The reaction mixture was stirred for 4 hours at −20° C. 20% ammonium chloride solution was added to the reaction mixture, which was then extracted with ethyl acetate. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 1.3 g of the titled compound as yellow solid.

後処理

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

出典と根拠

ORDレコード
ord-6c014da3c88f44b6b6f5e513eb99b976
出典データセット
uspto-grants-2010_02
特許番号
US07662832B2

反応ノート

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