Diisopropylethylamine → N-(4-bromobenzyl)-2-chloro-3,6-difluorobenzamide

HRID 1042930Notes

Reaction equation

HRID 1042930 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[Cl:11][C:12]1[C:20]([F:21])=[CH:19][CH:18]=[C:17]([F:22])[C:13]=1[C:14](O)=[O:15].C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:14](=[O:15])[C:13]2[C:17]([F:22])=[CH:18][CH:19]=[C:20]([F:21])[C:12]=2[Cl:11])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27240964-Bromobenzylamine hydrochlorideHCID 27735302-Chloro-3,6-difluorobenzoic acidHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium

Product 1

HCID 71150030N-(4-bromobenzyl)-2-chloro-3,6-difluorobenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-Bromophenyl)methanamine hydrochloride (0.5 g, 2.25 mmol), 2-chloro-3,6-difluorobenzoic acid (0.52 g, 2.7 mmol), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetra methyl uronium hexafluorophosphate methanaminium (HATU) (1.2 g, 2.7 mmol), and N,N-diisopropyl-ethylamine (1.17 mL, 6.75 mmol) were combined in DMF (6 mL) and then stirred at room temperature for 1 h. The reaction mixture was diluted in ethyl acetate and washed once with water and twice with an aqueous saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuum. The crude product was suspended in hot acetonitrile and then filtered to have the pure compound N-(4-bromobenzyl)-2-chloro-3,6-difluorobenzamide.

Workup

  1. washwashed once with water and twice with an aqueous saturated sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. filtrationfiltered

Sources & evidence

ORD record
ord-e1a7829133ef4c8cbffdba2ff19d546a
Source dataset
uspto-grants-2013_10
Patent number
US08558001B2

Reaction notes

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