Ethanol → HCID 57692982, compound

HRID 545588Notes

Reaction equation

HRID 545588 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[F:10].[NH2:11][C:12]1[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][C:13]=1B(O)O.C([O-])(=O)C.[K+].C(O)C>[Cl-].[Na+].O.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[NH2:11][C:12]1[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][C:13]=1[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[F:10]

Participants

7

Reactant 4

HCID 702EthanolHCID 517044Potassium AcetateHCID 2737801(2-Amino-4-(methoxycarbonyl)phenyl)boronic acidHCID 37184441-Bromo-2-fluoro-4-methoxybenzene

Product 1

HCID 57692982HCID 57692982, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

1-Bromo-2-fluoro-4-methoxybenzene (750 mg, 3.66 mmol), [2-amino-4-(methoxycarbonyl)phenyl]boronic acid (856 mg, 4.39 mmol), potassium acetate (3.66 mL, 2M aq, 7.32 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride dichloromethane adduct (299 mg, 10 mol. %) and ethanol (30 ml) were heated in an 80° C. oil bath for 3 hours. Reaction crude was worked up with brine, extracted with ethyl acetate, dried over Na2SO4, filtered and evaporated to afford a dark oil. This oil was purified by SiO2 (Biotage HorizonFlash system, 40+M cartridge, 0-25% EtOAc/hexanes, v/v) to afford the title compound as a yellow crystalline solid. LCMS calc.=275.10; found=276.09 (M+1)+.

Workup

  1. customReaction crude
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford a dark oil
  7. customThis oil was purified by SiO2 (Biotage HorizonFlash system, 40+M cartridge, 0-25% EtOAc/hexanes

Sources & evidence

ORD record
ord-bcfbcdb2a9e44ac7bd435d1131dcd25b
Source dataset
uspto-grants-2011_05
Patent number
US07935727B2

Reaction notes

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