HCID 178524742, compound → HCID 178516468, compound

HRID 1693689Notes

Reaction equation

HRID 1693689 reaction equation
[OH:1][C:2]1[C:7](C(O)=O)=[CH:6][N:5]=[C:4]2[NH:11][N:12]=[CH:13][C:3]=12>C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:11][N:12]=[CH:13][C:3]=12

Participants

3

Reactant 1

HCID 178524742HCID 178524742, compound

Product 1

HCID 178516468HCID 178516468, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An alternative synthesis of intermediates 19 has been described by Misra et al. (Bioorg. Med. Chem. Lett, Vol. 13(14), 2003, p. 2405). Suitably protected 4-Hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (22, Y═OH, Z═OH) can be decarboxylated at temperatures above 200° C. Bromination of the resulting 4-Hydroxy-1H-pyrazolo[3,4-b]pyridine using elemental bromine in ethanol affords 19a (X═OH). Chlorination using phosphorus oxychloride affords 5-bromo-4-chloro-1H-pyrazolo[3,4-b]pyridine 19b (X═Cl).

Workup

  1. customcan be decarboxylated at temperatures above 200° C

Sources & evidence

ORD record
ord-9349d82e00f140f9ad6b75f7ee78e8a3
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

Loading…