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Sodium Carbonate → HCID 178489326, compound

HRID 2234708
Notes
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Reaction equation

HRID 2234708 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:5]2=[N:6][CH:7]=1.[NH:29]1[CH:33]=[CH:32][C:31](B(O)O)=[N:30]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:33]3[CH:32]=[CH:31][NH:30][N:29]=3)[CH:3]=2)[N:8]([S:19]([C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)(=[O:21])=[O:20])[CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 59699754HCID 59699754, compoundHCID 178514837HCID 178514837, compound

Product 1

HCID 178489326HCID 178489326, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
165 °C

Procedure

5-Bromo-3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (200 mg, 0.438 mmol), commercial 1H-pyrazole-3-boronic acid (73.6 mg, 0.637 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichloromethane adduct (17.8 mg, 0.022 mmol) were combined in dimethylformamide (1.4 mL) and 2 M saturated sodium carbonate (657 μL) under nitrogen. The mixture was heated to 165° C. in the microwave for 900 s. The mixture was diluted with ethyl acetate and the aqueous layer was removed. After drying over sodium sulfate, the crude material was purified by silica gel chromatography to afford 3-(2-methoxy-phenyl)-5-(1H-pyrazol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (156 mg, 80.2%). %). MS: m/z 445 (M+H+).

Workup

  1. customthe aqueous layer was removed
  2. dry with materialAfter drying over sodium sulfate
  3. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-20c8568019e547a3969eadcc215f1113
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709645B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes