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

HRID 2241279Notes

Reaction equation

HRID 2241279 reaction equation
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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b0871fe7e0794d6491f611fd4ced8c18
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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