Sodium Carbonate → HCID 66747633, compound

HRID 2035952Notes

Reaction equation

HRID 2035952 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[F:7][C:8]1[N:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.Br[C:18]1[C:19]([NH2:24])=[N:20][CH:21]=[CH:22][CH:23]=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>[F:7][C:8]1[N:13]=[CH:12][C:11]([C:18]2[C:19]([NH2:24])=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 8177002-Amino-3-bromopyridineHCID 2783397(6-Fluoropyridin-3-yl)boronic acid

Product 1

HCID 66747633HCID 66747633, compoundYield 87.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of sodium carbonate (5.79 g), tetrakis(triphenylphosphine)palladium(0) (0.631 g), 6-fluoropyridin-3-ylboronic acid (5 g) and 3-bromopyridin-2-amine (4.72 g) in DME (75 mL) and water (15 ml) was stirred at 80° C. overnight. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane, then. NH silica gel, eluted with EtOAc in hexane) to give the title compound (4.53 g) as a colorless solid.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel
  7. washeluted with EtOAc in hexane
  8. washNH silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-77571b7a5c0e4b758ebee6fb4c09e3f2
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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