Sodium Carbonate → HCID 67145393, compound

HRID 2178742Notes

Reaction equation

HRID 2178742 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[Cl:12][C:13]1[CH:14]=[C:15](I)[C:16]([NH2:19])=[N:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:14]=[C:15]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[S:2][CH3:1])[C:16]([NH2:19])=[N:17][CH:18]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27735432-(Methylthio)benzeneboronic acidHCID 110760102-Amino-5-chloro-3-iodopyridine

Product 1

HCID 67145393HCID 67145393, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Mixture of 2-(methylthio)phenylboronic acid (5.0 g, 29.8 mmol), 5-chloro-3-iodopyridin-2-amine (7.56 g, 29.8 mmol), sodium carbonate (9.0 g, in 50 mL of water), Pd(PPh3)4 (621 mg) and 100 mL of toluene was refluxed overnight under N2. reaction mixture was cooled down to room temperature, organic layer was separated and concentrated in vacuum. The residue was subjected to column chromatography on silica gel with hexane/ethyl acetate gradient mixture as eluent, providing 3.5 g of 5-chloro-3-(2-(methylthio)phenyl)pyridin-2-amine.

Workup

  1. temperaturewas refluxed overnight under N2
  2. customreaction mixture
  3. customorganic layer was separated
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-3dff9ed32402442792153133afec4c56
Source dataset
uspto-grants-2015_06
Patent number
US09067947B2

Reaction notes

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