Dimethylformamide → [2-Bromo-5-(4-chlorophenyl)pyridin-3-yl]dimethylamine

HRID 734873ノート

反応式

HRID 734873 の反応式
[H-].[Na+].[Br:3][C:4]1C(N)=[CH:8][C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:6][N:5]=1.CI.[CH3:20][N:21]([CH:23]=O)[CH3:22]>C(=O)(O)[O-].[Na+]>[Br:3][C:4]1[C:23]([N:21]([CH3:22])[CH3:20])=[CH:8][C:7]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[CH:6][N:5]=1

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 859697042-Bromo-5-(4-chloro-phenyl)-pyridin-3-ylamine

生成物 1

HCID 86076948[2-Bromo-5-(4-chlorophenyl)pyridin-3-yl]dimethylamine

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

実験手順

169 mg (3.88 mmol) of sodium hydride (55% suspension) was added batchwise under a nitrogen atmosphere to a solution of 0.50 g (1.76 mmol) of 2-bromo-5-(4-chlorophenyl)pyridin-3-ylamine (Example 16.1c) in 10 mL of DMF and the mixture was stirred for 15 minutes at RT. A solution of 0.22 mL (3.53 mmol) of methyl iodide in 0.5 mL of DMF was added and the mixture was stirred for 16 hours at RT. The reaction mixture was diluted with semisaturated aqueous sodium bicarbonate solution and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with water, dried over magnesium sulfate, and evaporated down in vacuo. Yield: 0.47 g (85% of theoretical); C13H12BrClN2 (M=311.605); calc.: molpeak (M+H)+: 311/313/315 (BrCl); found: molpeak(M+H)+:311/313/315 (BrCl).

後処理

  1. stirringthe mixture was stirred for 16 hours at RT
  2. extractionthe aqueous phase was extracted with EtOAc
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down in vacuo

出典と根拠

ORDレコード
ord-4f2cf573d2a24d8880af039e1cb73627
出典データセット
uspto-grants-2009_09
特許番号
US07592358B2

反応ノート

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