Methyl iodide → 3-Bromo-6-methoxypyridin-2-amine

HRID 1848362ノート

反応式

HRID 1848362 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[Br:9].[C:10]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Br:9][C:3]1[C:2]([NH2:1])=[N:7][C:6]([O:8][CH3:10])=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178508959HCID 178508959、化合物

生成物 1

HCID 234358793-Bromo-6-methoxypyridin-2-amine収率 12.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Under an argon atmosphere 6-amino-5-bromo-pyridin-2-ol (23 g, 122 mmol) was dissolved in DMF (300 mL). K2CO3 (50.6 g, 366 mmol) was added followed by the addition of methyl iodide (11.4 mL, 183 mmol). The mixture was stirred for 4 h while keeping the temperature at 20-25° C. The suspension was poured onto H2O (1 L) and the aqueous phase was extracted with EtOAc (×2). The combined organic phases washed with H2O (0.5 L) and brine (200 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography, eluent toluene:heptane 2:1->100:0 followed by toluene:EtOAc 95:5 to afford 3-bromo-6-methoxy-pyridin-2-ylamine as a solid (3 g).

後処理

  1. customat 20-25° C
  2. additionThe suspension was poured onto H2O (1 L)
  3. extractionthe aqueous phase was extracted with EtOAc (×2)
  4. washThe combined organic phases washed with H2O (0.5 L) and brine (200 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography, eluent toluene:heptane 2:1->100:0

出典と根拠

ORDレコード
ord-c770a1b1092a44f2bb4fce3b0585347d
出典データセット
uspto-grants-2015_02
特許番号
US08952162B2

反応ノート

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