Dimethylformamide → 4-Bromo-N-(3-tert-butyl-phenyl)-3-fluoro-benzamide

HRID 2190537Notes

Reaction equation

HRID 2190537 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH2:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][C:14]=1[F:22].CN(C=O)C.CCN=C=NCCCN(C)C>C(Cl)Cl>[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=2)=[O:18])=[CH:15][C:14]=1[F:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 793343-tert-ButylanilineHCID 27733414-Bromo-3-fluorobenzoic acid

Product 1

HCID 593181654-Bromo-N-(3-tert-butyl-phenyl)-3-fluoro-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-tert-butyl-phenylamine was added 4-bromo-3-fluoro-benzoic acid, DMF (21 mL) and EDCI and were stirred at room temperature overnight. The reaction was diluted with DCM (8 mL) and was washed with HCl (1 M, 8 mL), NaOH (1 M, 8 mL), and brine (5 mL), dried over Na2SO4, and concentrated by stream of nitrogen. The resulting viscous oil was purified by flash chromatography with increasing concentration ethyl acetate in hexanes to afford the product. LCMS calcd for C17H17FNO (m/e) 349, obsd 350 (M+H).

Workup

  1. washwas washed with HCl (1 M, 8 mL), NaOH (1 M, 8 mL), and brine (5 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated by stream of nitrogen
  4. customThe resulting viscous oil was purified by flash chromatography
  5. temperaturewith increasing
  6. concentrationconcentration ethyl acetate in hexanes
  7. customto afford the product

Sources & evidence

ORD record
ord-32d0305ea5424f888bd1eb2c8a954617
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

Loading…