Trifluoroacetic acid → 4-Chloro-1H-pyrazolo[3,4-b]pyridine

HRID 1774708Notes

Reaction equation

HRID 1774708 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](CC3C=CC(OC)=CC=3)[N:9]=[CH:10][C:3]=12.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593985764-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 3100454-Chloro-1H-pyrazolo[3,4-b]pyridine

Procedure

4-Chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine (5) 19 g (69.4 mmol) in neat TFA (30 mL, 389 mmol) was stirred at 80° C. for 4 hr. The resulting RM was concentrated and MeOH was added and the obtained precipitate was filtered and washed with MeOH. The crude solid was treated with EtOAc, saturated NaHCO3 and dried over Na2SO4, to yield the desired product as a half white solid. 1H NMR (400 MHz, CDCl3): δ 13.23 (br s, 1H), 8.52 (d, J=5.1 Hz, 1H), 8.10 (s, 1H), 7.32 (m, 1H).

Workup

  1. concentrationThe resulting RM was concentrated
  2. additionMeOH was added
  3. filtrationthe obtained precipitate was filtered
  4. washwashed with MeOH
  5. additionThe crude solid was treated with EtOAc, saturated NaHCO3
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-9d48a8a26da34e98a568ed758723785f
Source dataset
uspto-grants-2016_02
Patent number
US09260426B2

Reaction notes

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