Sodium Carbonate → HCID 46317431, compound

HRID 2366470Notes

Reaction equation

HRID 2366470 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC.O.C(O)C>[F:12][C:4]1[CH:3]=[C:2]([C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 113453114-Bromo-2-fluoro-benzoic acid methyl ester

Product 1

HCID 46317431HCID 46317431, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Procedure

A mixture of EXAMPLE 50A (5 g), 3-pyridinylboronic acid (4 g) and dichlorobis(triphenylphosphine)-palladium (II) (1.1 g) in 7:3:2 DME/water/ethanol (200 mL) and 2M aqueous Na2CO3 solution (1 mL) at 80° C. was stirred 18 hours, cooled and filtered. The filtrate was partitioned between ethyl acetate and water, and the ethyl acetate layer washed with water and concentrated. The concentrate was flash chromatographed on silica gel with 1:2 ethyl acetate/hexanes.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customThe filtrate was partitioned between ethyl acetate and water
  4. washthe ethyl acetate layer washed with water
  5. concentrationconcentrated
  6. customchromatographed on silica gel with 1:2 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e8f2c6615365443fac76fa770a216954
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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