Diisopropylethylamine → HCID 59700969, compound

HRID 901985Notes

Reaction equation

HRID 901985 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([CH2:8][CH2:9][C:10]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:11]=2[C:12](O)=[O:13])[CH:7]=1.C([N:25](C(C)C)CC)(C)C>CN(C=O)C.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([CH2:8][CH2:9][C:10]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([NH2:25])=[O:13])[CH:7]=1

Participants

6

Reactant 2

HCID 81531DiisopropylethylamineHCID 59701029HCID 59701029, compound

Product 1

HCID 59700969HCID 59700969, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[2-(5-bromo-2-methoxyphenyl)-ethyl]-3-fluorobenzoic acid (1.78 g, 5.1 mol, 1 equiv) in DMF (6 mL) at room temperature were added diisopropylethylamine (DIPEA) (1.95 mL, 11.2 mmol, 2.2 equiv) and fluoro-N,N,N′-tetramethylformamidinium hexafluorophosphate (TFFH) (1.48 g, 5.6 mmol, 1.1 equiv). The homogeneous solution was allowed to stir for 1.5 hr, during which time the color changed to green. Ammonia gas was bubbled into the solution and the color changed to yellow and a precipitate was formed. The heterogeneous slurry was allowed to stir for 5 hr and then diluted with H2O and ethyl acetate. The phases were separated and the organic portion was washed with brine, dried over MgSO4, filtered and concentrated to give 2-[2-(5-bromo-2-methoxyphenyl)-ethyl]-3-fluorobenzamide in quantitative yield. The crude product was used without further purification. LCMS ES+ 352 (M+1), 354 (M+3).

Workup

  1. customAmmonia gas was bubbled into the solution
  2. customwas formed
  3. stirringto stir for 5 hr
  4. customThe phases were separated
  5. washthe organic portion was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6d64d8ae1add4590a7dded2f893d3b6f
Source dataset
uspto-grants-2008_04
Patent number
US07365070B2

Reaction notes

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