3'',5''-Difluoro-5'-nitro-3,2':3',4''-terpyridin-6'-amine → 3'',5''-Difluoro-3,2':3',4''-terpyridine-5',6'-diamine

HRID 2264196Notes

Reaction equation

HRID 2264196 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:24])[C:7]=1[C:8]1[C:9]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[N:10][C:11]([NH2:17])=[C:12]([N+:14]([O-])=O)[CH:13]=1>[Pd].C1COCC1.C(O)C>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:24])[C:7]=1[C:8]1[C:9]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[N:10][C:11]([NH2:17])=[C:12]([NH2:14])[CH:13]=1

Participants

4

Reactant 1

HCID 595959683'',5''-Difluoro-5'-nitro-3,2':3',4''-terpyridin-6'-amine

Product 1

HCID 595959713'',5''-Difluoro-3,2':3',4''-terpyridine-5',6'-diamineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A suspension of 3″,5″-difluoro-5′-nitro-3,2′:3′,4″-terpyridin-6′-amine (0.2 g, 0.608 mmol) and 10% palladium on carbon (0.04 g) in a mixture of THF/ethanol 40:60 (8 mL) was stirred under hydrogen atmosphere at 2.76 bar. After 12 h, the mixture was filtered through Celite® and the filter cake was washed with ethanol and THF. The combined filtrate and washings were evaporated to give the title compound as a solid (0.180 g, 99%).

Workup

  1. filtrationthe mixture was filtered through Celite®
  2. washthe filter cake was washed with ethanol and THF
  3. customThe combined filtrate and washings were evaporated

Sources & evidence

ORD record
ord-86d465353b0144cab9062f870e7fcc03
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

Loading…