HCID 86680626, compound → HCID 71547908, compound

HRID 1497457Notes

Reaction equation

HRID 1497457 reaction equation
[N:1]1([CH:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)=[CH:10][N:9]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1>C(OCC)(=O)C.[Pd]>[N:1]1([CH:6]([C:8]2[N:9]=[CH:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 86680626HCID 86680626, compound

Product 1

HCID 71547908HCID 71547908, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(1-(1H-imidazol-1-yl)ethyl)-5-(4-nitrophenyl)pyridine (255 mg, 0.86 mmol) in ethyl acetate (10 mL) was added 10% Pd/C (about 50 mg), under nitrogen. The reaction was stirred at rt for about 6 h under hydrogen. The reaction mixture was filtered through a Celite® bed and the filtrate was concentrated under vacuum to obtain crude product. The crude product was purified by prep TLC method using 3% methanol in DCM to provide 4-(6-(1-(1H-imidazol-1-yl)ethyl)pyridin-3-yl)aniline as off white solid (160 mg, 70% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.71 (d, 1H), 7.87 (dd, 1H), 7.78 (s, 1H), 7.36 (d, 2H), 7.24 (s, 1H), 7.14 (d, 1H), 6.88 (s, 1H), 6.61 (t, 2H), 5.60-5.54 (m, 1H), 5.29 (s, 2H), 1.79 (d, 2H), LC-MS m/z calcd for [M+H]+ 265.14. found 265.4.

Workup

  1. filtrationThe reaction mixture was filtered through a Celite® bed
  2. concentrationthe filtrate was concentrated under vacuum
  3. customto obtain crude product
  4. customThe crude product was purified by prep TLC method

Sources & evidence

ORD record
ord-9792652b352e416fbe316f60a85168a1
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

Loading…