Ethanol ethylacetate → 6-ethyl-N2,N2-di-BOC-4,4'-bipyridine-2,3'-diamine

HRID 69970Notes

Reaction equation

HRID 69970 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][C:24]=2[N+:29]([O-])=O)[CH:3]=1.[CH3:32]CO.CCOC(C)=O>[Pd]>[CH2:1]([C:2]1[N:7]=[C:6]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][C:24]=2[NH2:29])[CH:3]=1)[CH3:32]

Participants

4

Reactant 2

HCID 21584252Ethanol ethylacetateHCID 690441506-methyl-N,N-di-BOC-3'-nitro-4,4'-bipyridin-2-amine

Product 1

HCID 690438626-ethyl-N2,N2-di-BOC-4,4'-bipyridine-2,3'-diamineYield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 6-methyl-N,N-di-BOC-3′-nitro-4,4′-bipyridin-2-amine in EtOH/EtOAc (1:1, 0.2M) was added Pd/C (10% by weight) and the reaction was stirred under a H2 balloon for 18 hrs. Filtered through Celite, washed with EtOAc and concentrated the filtrate to afford 6-ethyl-N2,N2-di-BOC-4,4′-bipyridine-2,3′-diamine in >95% yield. LCMS (m/z): 401.0 (MH+); LC Rt=2.81 min.

Workup

  1. filtrationFiltered through Celite
  2. washwashed with EtOAc
  3. concentrationconcentrated the filtrate

Sources & evidence

ORD record
ord-edff22bbb28244fbadf699577559d609
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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