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Dimethylformamide → 1-(4-methoxybenzyl)-4-(5-chloro-2-fluoro-4-nitrophenoxy)-3-iodo-1H-pyrazolo[3,4-b]pyridine

HRID 2241384
Notes
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Reaction equation

HRID 2241384 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][O:14][C:15]1[CH:32]=[CH:31][C:18]([CH2:19][N:20]2[C:24]3[N:25]=[CH:26][CH:27]=[C:28]([OH:29])[C:23]=3[C:22]([I:30])=[N:21]2)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]2[C:24]3=[N:25][CH:26]=[CH:27][C:28]([O:29][C:6]4[CH:7]=[C:2]([Cl:1])[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][C:5]=4[F:9])=[C:23]3[C:22]([I:30])=[N:21]2)=[CH:31][CH:32]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 101303301-Chloro-4,5-difluoro-2-nitrobenzeneHCID 178490915HCID 178490915, compound

Product 1

HCID 685164081-(4-methoxybenzyl)-4-(5-chloro-2-fluoro-4-nitrophenoxy)-3-iodo-1H-pyrazolo[3,4-b]pyridineYield 40.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-chloro-4,5-difluoro-2-nitrobenzene (2.23 g, 11.5 mmol), 1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-ol (4.00 g, 10.5 mmol), K2CO3 (1.60 g, 11.5 mmol) and DMF (100 mL) was heated to 50° C. for 18 hours. The reaction was cooled to ambient temperature, diluted with water (500 mL), extracted with EtOAc, dry over sodium sulfate, filter and concentrate. The residue was purified by flash column chromatography (5% MeOH in CH2Cl2) to provide a light pink solid. The solid was triturated with hot MeOH to afford the product (2.35 g, 40% yield) as a white solid. LRMS (APCI pos) m/e 554.8 (M+H).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. extractionextracted with EtOAc
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customThe residue was purified by flash column chromatography (5% MeOH in CH2Cl2)
  7. customto provide a light pink solid
  8. customThe solid was triturated with hot MeOH

Sources & evidence

ORD record
ord-5d51f60b41bb45beb51b2bd2c94845ed
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07723330B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes