Diisopropylethylamine → HCID 68521412, compound

HRID 1437435Notes

Reaction equation

HRID 1437435 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[F:12].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([NH2:22])[CH3:21])=[CH:16][CH:15]=1.CCN(C(C)C)C(C)C>CCCCO>[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:22][C@H:20]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[CH3:21])[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27362864-Bromo-2,5-difluoronitrobenzeneHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamine

Product 1

HCID 68521412HCID 68521412, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 1-bromo-2,5-difluoro-4-nitrobenzene (0.464 g, 1.95 mmol), (S)-1-(4-fluoro-phenyl)-ethylamine (0.298 g, 2.14 mmol), and DIEA (0.41 ml, 2.34 mmol) in n-BuOH (5 ml) was heated at 80° C. for 17 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane:EtOAc=5:1) to give the title compound as a yellow solid (0.63 g, 96%). NMR (400 MHz, CDCl3) 8.23 (br, 1H), 7.95 (d, J=8.8 Hz, 1H), 7.29 (m, 2H), 7.08 (m, 2H), 6.84 (d, J=5.6 Hz, 1H), 4.62 (m, 1H), 1.63 (d, J=6.8 Hz, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (hexane:EtOAc=5:1)

Sources & evidence

ORD record
ord-bb45a7f9754a4b85a6712c3d403b2f1a
Source dataset
uspto-grants-2009_11
Patent number
US07622482B2

Reaction notes

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