Phosphorus oxychloride → Ethyl 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 1471807Notes

Reaction equation

HRID 1471807 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]2[C:12]3[NH:13][CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16](=O)[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:27]>>[Cl:27][C:16]1[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][N:13]=[C:12]2[N:8]([CH2:7][C:6]3[CH:23]=[CH:24][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:9]=[CH:10][C:11]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135741690HCID 135741690, compound

Product 1

HCID 53665897Ethyl 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Procedure

Ethyl 1-(4-methoxybenzyl)-4-oxo-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 2 and POCl3 were heated at 80° C. in a sealed tube for 3 hours. Reaction mixture was concentrated in vacuo, diluted with diethylether, washed with water, dried over sodium sulfate and concentrated in vacuo to afford product 3 as off white solid.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. additiondiluted with diethylether
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8310c4405264e27beb553b2b549f5dc
Source dataset
uspto-grants-2015_04
Patent number
US09012470B2

Reaction notes

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