Sodium Carbonate → HCID 86602535, compound

HRID 494679Notes

Reaction equation

HRID 494679 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])=[C:17]([CH3:29])[CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[F:25][C:24]([F:26])([F:27])[C:23]([NH:22][C:18]1[C:19]([CH3:21])=[CH:20][C:15]([C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[CH:16][C:17]=1[CH3:29])=[O:28]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 17334921HCID 17334921, compound

Product 1

HCID 86602535HCID 86602535, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A two-neck 100 ml round bottom flask equipped with a reflux condenser capped with a three-way stopcock was charged with 4-tert-butylphenylboronic acid (0.841 g, 4.724 mmol), N-(4-bromo-2,6-dimethylphenyl)-2,2,2-trifluoroacetamide (1.3346 g, 4.73 mmol), Pd(OAc)2 (45 mg, 0.2 mmol), and Na2CO3 (1.009 g, 3.53 mmol). The reactor was purged of air (three vacuum/argon cycles) before degassed methanol (50 ml) was added. The reaction flask was placed in an ultrasound bath for 4.5 h. The solution was filtered on celite and evaporated. The residue was dissolved in 20 ml of CHCl3 and washed twice with water. The organic layer was dried over MgSO4, filtered and evaporated. The crude product was recrystallized from a CHCl3/hexane mixture to afford 2,2,2-trifluoro-N-(4′-tert-butyl-3,5-dimethyl-biphenyl-4-yl)-acetamide as a white grey solid in 74% yield. 1H NMR (CDCl3): δ=1.36 (s, 9H, C(CH3)3); 2.28 (s, 6H, ortho-CH3); 7.30-7.31 (d, 2H, CHar); 7.44-7.50 (m, 4H, CHar).

Workup

  1. customA two-neck 100 ml round bottom flask equipped with a reflux condenser
  2. customcapped with a three-way stopcock
  3. customThe reactor was purged of air (three vacuum/argon cycles)
  4. custombefore degassed methanol (50 ml)
  5. additionwas added
  6. filtrationThe solution was filtered on celite
  7. customevaporated
  8. dissolutionThe residue was dissolved in 20 ml of CHCl3
  9. washwashed twice with water
  10. dry with materialThe organic layer was dried over MgSO4
  11. filtrationfiltered
  12. customevaporated
  13. customThe crude product was recrystallized from a CHCl3/hexane mixture

Sources & evidence

ORD record
ord-a1eb17beda694785aa2eaae66db9b8b9
Source dataset
uspto-grants-2009_05
Patent number
US07538172B2

Reaction notes

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