4-Fluoroaniline → 2-azido-4-bromo-N-(4-fluorophenyl)-benzamide

HRID 1037558Notes

Reaction equation

HRID 1037558 reaction equation
[N:1]([C:4]1[CH:12]=[C:11]([Br:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)=[N+:2]=[N-:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[F:47][C:48]1[CH:54]=[CH:53][C:51]([NH2:52])=[CH:50][CH:49]=1>CN(C=O)C.O>[N:1]([C:4]1[CH:12]=[C:11]([Br:13])[CH:10]=[CH:9][C:5]=1[C:6]([NH:52][C:51]1[CH:53]=[CH:54][C:48]([F:47])=[CH:49][CH:50]=1)=[O:8])=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 97314-FluoroanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 860515482-Azido-4-bromobenzoic acid

Product 1

HCID 866664212-azido-4-bromo-N-(4-fluorophenyl)-benzamideYield 91.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of compound (xi) (15 g, 61.98 mmol) in DMF (150 mL) was added HATU (28.28 g, 74.34 mmol) at 0° C. The reaction mixture was stirred for 15 min and DIPEA (16.01 mL, 92.26 mmol) was added followed by 4-fluoroaniline (7.57 g, 68.68 mmol) at the same temperature. The reaction mixture was allowed to warm to RT and stirring was continued for 16 h. The reaction was then poured into cold water (500 mL) and stirred for 15 min. The solid was filtered and washed with water (3×100 mL) and dried (Na2SO4) to give 2-azido-4-bromo-N-(4-fluorophenyl)-benzamide (xii) (19 g, 91%) as an off-white solid.

Workup

  1. stirringstirring
  2. waitwas continued for 16 h
  3. stirringstirred for 15 min
  4. filtrationThe solid was filtered
  5. washwashed with water (3×100 mL)
  6. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-0472fff3a68e4da7a82a016b8149fc49
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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