Pyridine → 6-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]-3-cyanopyridazine

HRID 1870771ノート

反応式

HRID 1870771 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[N:16]=[N:15][C:14]([C:17]([NH2:19])=O)=[CH:13][CH: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[N:16]=[N:15][C:14]([C:17]#[N:19])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

参加物

5

反応物 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 186932416-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-pyridazine-3-carboxamide

生成物 1

HCID 226225146-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]-3-cyanopyridazine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The phenol from the previous step (1.73 g, 4.9 mmol) in THF (30 ml) was treated with pyridine (0.82 ml, 0.82 g, 10.2 mmol) followed by trifluoroacetic anhydride (1.61 ml, 2.42 g, 11.5 mmol). The mixture turned dark green and was left overnight at ambient temperature. The mixture was then evaporated to a gum, treated with an excess of an aqueous solution of sodium bicarbonate and stirred at ambient temperature for approximately 30 minutes. The resultant red solid was filtered, washed with water and sucked dry (1.8 g) and purified by MPLC to give 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-3-cyanopyridazine (as a white solid (0.87 g, 53%).

後処理

  1. customThe mixture was then evaporated to a gum
  2. additiontreated with an excess of an aqueous solution of sodium bicarbonate
  3. filtrationThe resultant red solid was filtered
  4. washwashed with water
  5. customsucked dry (1.8 g)
  6. custompurified by MPLC

出典と根拠

ORDレコード
ord-32b819612ff54f16a31f323145559fb9
出典データセット
uspto-grants-2000_08
特許番号
US06100258

反応ノート

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