Sodium Carbonate → HCID 66748566, compound

HRID 1405892Notes

Reaction equation

HRID 1405892 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][C:8]1[CH:9]=[C:10](B(O)O)[CH:11]=[CH:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16].Br[C:22]1[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=1>COCCOC.O.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>[Cl:7][C:8]1[CH:9]=[C:10]([C:22]2[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 8177002-Amino-3-bromopyridineHCID 33824673-Chloro-4-isopropoxyphenylboronic acid

Product 1

HCID 66748566HCID 66748566, compoundYield 81.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of sodium carbonate (760 mg), tetrakis(triphenylphosphine)palladium(0) (207 mg), 3-chloro-4-isopropoxyphenylboronic acid (1.00 g) and 3-bromopyridin-2-amine (621 mg) in DME (10 mL) and water (3 mL) was stirred at 80° C. overnight. The mixture was added with silica gel, concentrated in vacuo, and purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (770 mg) as a pale yellow solid.

Workup

  1. additionThe mixture was added with silica gel
  2. concentrationconcentrated in vacuo
  3. custompurified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-a3119656b0984619b1413da33acf3dcf
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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