Diisopropylamine → HCID 59375165, compound

HRID 1811054Notes

Reaction equation

HRID 1811054 reaction equation
[Br:1][C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[NH:5][CH3:6].C(NC(C)C)(C)C.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>C(Cl)Cl>[Br:1][C:2]1[C:3]([F:10])=[C:4]([N:5]([CH3:6])[C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:19]([F:18])=[CH:20][CH:21]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 678794-Fluorobenzoyl chlorideHCID 66606141HCID 66606141, compound

Product 1

HCID 59375165HCID 59375165, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 3 A solution of 3-bromo-2-fluoro-N-methylaniline (32 mg, 0.157 mmol) and diisopropylamine (0.055 mL, 0.314 mmol) in DCM (2 mL) was treated with 4-fluorobenzoyl chloride (0.028 mL, 0.235 mmol) and the mixture was stirred at rt for 2 h. The mixture was partitioned between DCM and NaHCO3 (aq). The organic phase was washed with brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 90:10 to 80:20 hexane-EtOAc) to provide N-(3-bromo-2-fluorophenyl)-4-fluoro-N-methylbenzamide as a white solid (35 mg, 68%). Mass spectrum m/z 326, 328 (M+H)+.

Workup

  1. customThe mixture was partitioned between DCM and NaHCO3 (aq)
  2. washThe organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (
  6. washeluting with a gradient from 90:10 to 80:20 hexane-EtOAc)

Sources & evidence

ORD record
ord-86459f871ab3403db80d7ff7e1d06d73
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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