Triethylamine → Methyl 3-{[[(3-bromo-4-fluorophenyl)methyl](methyl)amino]carbonyl}benzoate

HRID 564525Notes

Reaction equation

HRID 564525 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][CH3:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([OH:21])=O)=[O:15].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]([CH3:11])[C:19]([C:18]2[CH:17]=[C:16]([CH:24]=[CH:23][CH:22]=2)[C:14]([O:13][CH3:12])=[O:15])=[O:21])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16781426[(3-Bromo-4-fluorophenyl)methyl](methyl)amine

Product 1

HCID 57813368Methyl 3-{[[(3-bromo-4-fluorophenyl)methyl](methyl)amino]carbonyl}benzoateYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(3-bromo-4-fluorophenyl)methyl]methylamine (0.355 g, 1.63 mmol) in THF (16 mL) was added 3-[(methyloxy)carbonyl]benzoic acid (0.294 g, 1.63 mmol), HBTU (0.929 g, 2.45 mmol), Et3N (0.458 mL, 3.26 mmol) and stirred at room temperature for 65 h, and then quenched with H2O. The organic layer was loaded onto silica gel cartridge and purified by CombiFlash chromatograph to afford the title compound 0.419 g (68%). LC-MS m/z 380 (M+H)+.

Workup

  1. customquenched with H2O
  2. custompurified by CombiFlash chromatograph

Sources & evidence

ORD record
ord-8ae4e70cfc124837a350a017d30c2134
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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