Potassium Carbonate → N-[4-(2-tert-butoxy-pyridin-4-yl)-benzyl]-2,6-dichloro-benzamide

HRID 1042927Notes

Reaction equation

HRID 1042927 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[C:29]1[CH:34]=[CH:33][N:32]=[C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH:30]=1>CN(C=O)C.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]>[C:36]([O:35][C:31]1[CH:30]=[C:29]([C:11]2[CH:12]=[CH:13][C:8]([CH2:7][NH:6][C:4](=[O:5])[C:3]3[C:2]([Cl:1])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:21])=[CH:9][CH:10]=2)[CH:34]=[CH:33][N:32]=1)([CH3:39])([CH3:37])[CH3:38]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 457878724-Bromo-2-tert-butoxypyridineHCID 711499724-[(2,6-Dichloro-benzoylamino)methyl]phenylboronic acid

Product 1

HCID 71149992N-[4-(2-tert-butoxy-pyridin-4-yl)-benzyl]-2,6-dichloro-benzamide

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

4-[(2,6-Dichloro-benzoylamino)methyl]phenylboronic acid (5 g, 15.4 mmol), potassium carbonate (5 g), and [1,1′bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.56 g, 0.77 mmol) were combined in a round bottom flask. 4-Bromo-2-(t-butoxy)pyridine (3.55 g, 15.4 mmol) was dissolved in 20 mL DMF and added to the flask under stirring. The flask was flushed with nitrogen and 10 mL water was added. The reaction mixture was stirred at 70° C. for two hours. After cooling the mixture was poured into 300 mL ethyl acetate and washed with water and brine. The organic phase was dried with magnesium sulfate and evaporated under vacuum. The crude N-[4-(2-tert-butoxy-pyridin-4-yl)-benzyl]-2,6-dichloro-benzamide was further purified by silica gel chromatography (eluent: hexone/ethyl acetate 1:1).

Workup

  1. additionadded to the flask
  2. customThe flask was flushed with nitrogen and 10 mL water
  3. additionwas added
  4. stirringThe reaction mixture was stirred at 70° C. for two hours
  5. temperatureAfter cooling the mixture
  6. additionwas poured into 300 mL ethyl acetate
  7. washwashed with water and brine
  8. dry with materialThe organic phase was dried with magnesium sulfate
  9. customevaporated under vacuum
  10. customThe crude N-[4-(2-tert-butoxy-pyridin-4-yl)-benzyl]-2,6-dichloro-benzamide was further purified by silica gel chromatography (eluent: hexone/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-07ce29d136a6489fa0140dadfffe5465
Source dataset
uspto-grants-2013_10
Patent number
US08558001B2

Reaction notes

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