(2-Methoxypyridin-3-yl)boronic acid → HCID 69300355, compound

HRID 2218125Notes

Reaction equation

HRID 2218125 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[O:10])=[CH:4][C:3]=1[F:19].[CH3:20][O:21][C:22]1[C:27](B(O)O)=[CH:26][CH:25]=[CH:24][N:23]=1>CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+].O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:19][C:3]1[CH:4]=[C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[O:10])[CH:6]=[CH:7][C:2]=1[C:27]1[C:22]([O:21][CH3:20])=[N:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 2

HCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 69301564HCID 69301564, compound

Product 1

HCID 69300355HCID 69300355, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

1,1′-Bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.1 g) was added to a stirred and degassed solution of 1-(4-bromo-3-fluorophenyl)-3-o-tolylurea (0.5 g, 1.5 mmol) and 2-methoxypyrid-3-ylboronic acid (258 mg, 1.7 mmol) in dimethyl formamide (10 mL) and aqueous sodium carbonate in water (5 mL, 2N). The reaction mixture was stirred at 100° C. for 18 hours, then allowed to cool. The solution was concentrated, then ethyl acetate (75 mL) was added and the organic phase was washed with water (3×75 mL). The organic phase was dried (anhydrous magnesium sulfate), concentrated and purified by chromatography on silica gel (20 to 40% v/v ethyl acetate in hexane) to afford the title compound as an oil.

Workup

  1. stirringThe reaction mixture was stirred at 100° C. for 18 hours
  2. temperatureto cool
  3. concentrationThe solution was concentrated
  4. additionethyl acetate (75 mL) was added
  5. washthe organic phase was washed with water (3×75 mL)
  6. dry with materialThe organic phase was dried (anhydrous magnesium sulfate)
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel (20 to 40% v/v ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d0fe7f9b2b6a45c093b9cec0dfb6b05f
Source dataset
uspto-grants-2008_08
Patent number
US07410984B2

Reaction notes

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