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Toluene → HCID 68736170, compound

HRID 1514017
Notes
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Reaction equation

HRID 1514017 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[NH2:12][C:13]1[C:14](Br)=[N:15][CH:16]=[CH:17][CH:18]=1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:14]1[C:13]([NH2:12])=[CH:18][CH:17]=[CH:16][N:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 1140TolueneHCID 6428163-Amino-2-bromopyridineHCID 27735432-(Methylthio)benzeneboronic acidHCID 22031701Potassium phosphate, tribasic, monohydrate

Product 1

HCID 68736170HCID 68736170, compoundYield 78.4%

Reagents, catalysts & solvents 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalyst
HCID 962WaterSolvent

Procedure

The 500 mL round-bottom flask, equipped with magnetic stirrer and reflux condenser was charged with 2-(methylthio)phenylboronic acid (9.48 g, 56 mmol), 3-amino-2-bromopyridine (7.15 g, 57 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 0.92 g, 4 mol %), Pd2(dba)3 (1.02 g, 2 mol %), potassium phosphate hydrate (39 g, 3 equivalents), 100 mL of toluene. The flask was filled with nitrogen and heated to reflux under nitrogen atmosphere for 24 hours. Then the reaction was cooled down to room temperature, diluted with 500 ml of water and extracted with ethyl acetate (5×40 mL). Organic fractions were combined, dried over sodium sulfate, filtered and evaporated. The residue was subjected to column chromatography on silica gel with eluent hexane/ethyl acetate gradient mixture, providing 2-(2-(methylthio)phenyl)pyridin-3-amine as yellow crystals (9.5 g). NMR confirmed the structure.

Workup

  1. customThe 500 mL round-bottom flask, equipped with magnetic stirrer
  2. temperaturereflux condenser
  3. additionThe flask was filled with nitrogen
  4. temperatureheated
  5. temperatureto reflux under nitrogen atmosphere for 24 hours
  6. extractionextracted with ethyl acetate (5×40 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-c8b8bad228ae44208baff98433ad9c39
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08221905B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes