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

HRID 1870760노트

반응식

HRID 1870760 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>O1CCCC1>[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 1049Pyridine2회HCID 9845Trifluoroacetic anhydride2회HCID 183577602-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxamide

생성물 1

HCID 183577802-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-cyanopyridine수율 105.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

2-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxamide (example 4) (1.0 g, 2.85 mmol) was suspended in tetrahydrofuran (15 ml) and the stirred solution treated with pyridine (0.46 ml, 0.46 g, 5.7 mmol) and trifluoroacetic anhydride (0.9 ml, 1.35 g, 6.4 mmol) at ambient temperature (slight exotherm). A yellow colour became apparent and the solid dissolved in the THF. The solution was left standing at ambient temperature overnight, then further pyridine (0.46 ml, 5.7 mmol) and TFAA (0.90 ml, 6.4 mmol) were added and the reaction was again left overnight. The mixture was evaporated to low volume, saturated sodium bicarbonate solution was added and the mixture stirred at ambient temperature for 30 minutes, evaporated to low volume and the resultant white precipitate filtered, washed with water and air dried to give 2-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-cyanopyridine as a white solid (1.0 g, 100%).

후처리

  1. waitThe solution was left
  2. waitthe reaction was again left overnight
  3. customThe mixture was evaporated to low volume, saturated sodium bicarbonate solution
  4. additionwas added
  5. customevaporated to low volume
  6. filtrationthe resultant white precipitate filtered
  7. washwashed with water and air
  8. customdried

출처 및 근거

ORD 기록
ord-067c319844a24c209c6e05793cc8e483
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06100258

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