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

HRID 1870762노트

반응식

HRID 1870762 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0e34099c7e484ae093f2f2f157af7192
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06100258

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