Trifluoroacetic acid → 4-(5-chloro-2-methyl-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine

HRID 2241279노트

반응식

HRID 2241279 반응식
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[C:22]([Cl:24])[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][C:19]=4[CH3:28])=[C:11]3[CH:10]=[N:9]2)=CC=1.FC(F)(F)C(O)=O>>[Cl:24][C:22]1[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][C:19]([CH3:28])=[C:18]([CH:23]=1)[O:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:8][N:9]=[CH:10][C:11]=12

참가 물질

3

반응물 2

HCID 6422Trifluoroacetic acidHCID 685114941-(4-methoxybenzyl)-4-(5-chloro-2-methyl-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine

생성물 1

HCID 685159114-(5-chloro-2-methyl-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine

실험 절차

1-(4-Methoxybenzyl)-4-(5-chloro-2-methyl-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine (42 g, 98.9 mmol) and 2,2,2-trifluoroacetic acid (76.2 ml, 989 mmol) were stirred at reflux for 4 h. The reaction was concentrated in vacuo, using toluene to azeotrope. The residue was diluted with EtOAc and saturated NaHCO3 was added to neutralize the acid, and the resulting suspension was stirred for 20 minutes. The precipitate was filtered and washed with water to remove residual NaHCO3. The solid was further dried by toluene azeotrope. The tan solid was left under high vacuum for 18 hours. The product (22 g, 70%) was carried forward without further purification.

후처리

  1. temperatureat reflux for 4 h
  2. concentrationThe reaction was concentrated in vacuo
  3. additionThe residue was diluted with EtOAc and saturated NaHCO3
  4. additionwas added
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customto remove residual NaHCO3
  8. dry with materialThe solid was further dried by toluene azeotrope
  9. waitThe tan solid was left under high vacuum for 18 hours
  10. customThe product (22 g, 70%) was carried forward without further purification

출처 및 근거

ORD 기록
ord-b0871fe7e0794d6491f611fd4ced8c18
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723330B2

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