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Water → Ethyl-4-ethoxy-1-(pent-4-ynyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 1252700
Notes
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Reaction equation

HRID 1252700 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=[C:6]2[NH:15][N:16]=[CH:17][C:5]=12)[CH3:2].I[CH2:19][CH2:20][CH2:21][C:22]#[CH:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:13]([O:12][C:10]([C:9]1[C:4]([O:3][CH2:1][CH3:2])=[C:5]2[CH:17]=[N:16][N:15]([CH2:23][CH2:22][CH2:21][C:20]#[CH:19])[C:6]2=[N:7][CH:8]=1)=[O:11])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 110197205-Iodo-1-pentyneHCID 14590535CID 14590535

Product 1

HCID 20139384Ethyl-4-ethoxy-1-(pent-4-ynyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylateYield 111.9%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of 3.78 g of ethyl 4-ethoxy-1H-pyrazolo-[3,4-b]pyridine-5-carboxylate, 3.90 g of 1-iodo-4-pentyne, and 6.68 g of pulverized anhydrous potassium carbonate in 27 ml of dry DMF was stirred at 50°-60° for 1 hr. The mixture was cooled, poured into water, and the resulting mixture extracted with EtOAc. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated to leave 5.42 g of a dark oil which slowly crystallized. This material was chromatographed over silica gel using EtOAc/hexane 1:2 (v/v) as the eluant to give 3.03 g (62%) of the title compound as a white solid. A small quantity was recrystallized from toluene to give white crystals, m.p. 84°-85.5°.

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe resulting mixture extracted with EtOAc
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f6bfb04c757b4e6fb17edb4ba061a7f5
Source dataset
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04745121

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes