Pyridine → 2-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-cyanopyridine

HRID 427754ノート

反応式

HRID 427754 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([NH2:19])=O)=[CH:13][N:12]=1)[CH2:9][CH3:10].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:19])=[CH:13][N:12]=1)[CH2:9][CH3:10]

参加物

5

反応物 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 183577602-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxamide

生成物 1

HCID 183577802-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-cyanopyridine収率 63%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxamide (example 4) (1.93 g, 5.5 mmol) was suspended in THF (30 ml) and treated with pyridine (1.15 g, 14.25 mmol, 1.15 ml) followed by trifluoroacetic anhydride (3.4 g, 16 mmol) whilst stirring at ambient temperature. The white solid dissolved and there was a slight exotherm. The resultant solution was left overnight at ambient temperature. The mixture was then evaporated to low volume, a saturated aqueous solution of sodium bicarbonate was added and the mixture stirred at ambient temperature for 30 minutes. The mixture was again evaporated to low volume and the white solid that precipitated was filtered, washed with water and sucked dry (1.68 g). The solid was purified by MPLC on silica to give 2-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-cyanopyridine as a white solid (1.15 g, 63%).

後処理

  1. dissolutionThe white solid dissolved
  2. customThe mixture was then evaporated to low volume
  3. additiona saturated aqueous solution of sodium bicarbonate was added
  4. stirringthe mixture stirred at ambient temperature for 30 minutes
  5. customThe mixture was again evaporated to low volume
  6. customthe white solid that precipitated
  7. filtrationwas filtered
  8. washwashed with water
  9. customsucked dry (1.68 g)
  10. customThe solid was purified by MPLC on silica

出典と根拠

ORDレコード
ord-964c3fbe30444177b0588093a0cf6655
出典データセット
uspto-grants-2001_11
特許番号
US06313148B1

反応ノート

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