Diisopropylethylamine → N1-(4-Bromobenzyl)-5-((5-methylpyridin-2-yl)methoxy)benzene-1,2-diamine

HRID 1527731Notes

Reaction equation

HRID 1527731 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=3)[CH:11]=[CH:10][C:9]=2[N+:23]([O-])=O)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C>C1COCC1.[Pt]>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]2[C:9]([NH2:23])=[CH:10][CH:11]=[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=3)[CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 90410173N-(4-Bromobenzyl)-5-((5-methylpyridin-2-yl)methoxy)-2-nitroaniline

Product 1

HCID 117607702N1-(4-Bromobenzyl)-5-((5-methylpyridin-2-yl)methoxy)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-bromobenzyl)-5-((5-methylpyridin-2-yl)methoxy)-2-nitroaniline (4.1 g, 9.6 mmol) in THF (75 mL) was added DIPEA (0.8 mL, 4.8 mmol) followed by 5% platinum on carbon (0.4 g, 2.1 mmol). The reaction vessel was evacuated and then placed under 1 atmosphere of H2 for 6 h. The mixture was then flushed with N2 and filtered through a pad of Celite. The Celite was rinsed with THF. The resulting filtrate was concentrated to dryness to afford the title compound, which was used without further purification. MS (ESI): mass calcd. for C22H26BrN3O, 397.08; m/z found, 398.0 [M+H]+.

Workup

  1. customThe reaction vessel was evacuated
  2. customThe mixture was then flushed with N2
  3. filtrationfiltered through a pad of Celite
  4. washThe Celite was rinsed with THF
  5. concentrationThe resulting filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-2580afa6e55644f183df53c60aac1f57
Source dataset
uspto-grants-2015_07
Patent number
US09089569B2

Reaction notes

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