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

HRID 1932313ノート

反応式

HRID 1932313 の反応式
[CH3:1][C:2]([Mg]Br)=[CH:3][CH3:4].[F:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][CH2:13][C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:10][CH:9]=1.[Cl-].[NH4+]>O1CCCC1>[F:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][CH2:13][C:14]2[N:15]=[CH:16][CH:17]=[C:18]3[C:3]([CH3:4])=[C:2]([CH3:1])[NH:20][C:19]=23)=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 671428762-(4-Fluorophenoxymethyl)-3-nitropyridineHCID 178448414HCID 178448414、化合物

生成物 1

HCID 116087297-(4-fluorophenoxymethyl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine収率 19.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1-Methyl-1-propenyl magnesium bromide (0.5 M in tetrahydrofuran solution, 1.7 ml, 0.851 mmol) was added at −78° C. to a solution of 2-(4-fluorophenoxymethyl)-3-nitropyridine (71 mg, 0.284 mmol) prepared in Preparation 1 in anhydrous tetrahydrofuran (5 ml). The reaction mixture was stirred overnight and a saturated ammonium chloride solution was added thereto. The reaction mixture was extracted with ethyl acetate (15 ml). The organic layer was washed with water (5 ml), dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (dichloromethane/n-hexane=2/1, v/v) to give 15 mg of the titled compound as brown oil.

後処理

  1. extractionThe reaction mixture was extracted with ethyl acetate (15 ml)
  2. washThe organic layer was washed with water (5 ml)
  3. dry with materialdried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography (dichloromethane/n-hexane=2/1

出典と根拠

ORDレコード
ord-aa1872dfd3ab4b78bcdcb343aefa31a6
出典データセット
uspto-grants-2012_05
特許番号
US08188114B2

反応ノート

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