HCID 21875925, compound → HCID 21876246, compound

HRID 1454604Notes

Reaction equation

HRID 1454604 reaction equation
[CH2:1]([C:3]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][N:22]=[N+]=[N-])=[CH:16][CH:15]=2)[C:6]2=[N:7][C:8]([Cl:12])=[C:9]([Cl:11])[CH:10]=[C:5]2[N:4]=1)[CH3:2]>CO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH2:1]([C:3]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:22])=[CH:16][CH:15]=2)[C:6]2=[N:7][C:8]([Cl:12])=[C:9]([Cl:11])[CH:10]=[C:5]2[N:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 21875925HCID 21875925, compound

Product 1

HCID 21876246HCID 21876246, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(2-ethyl-5,6-dichloro-3H-imidazo[4,5-b]pyridin-3-yl)phenyl]ethyl azide (step 6, 69 mg, 0.2 mmol) in methanol (10 mL) was added Lindlar catalyst (5 mg). The resulting mixture was stirred for 6 h under hydrogen atmosphere. The mixture was filtered through a pad of Celite and the filtrate was concentrated. Purification by preparative TLC (dichloromethane/methanol=10:1) gave 60 mg (94%) of the title compound as colorless solids: MS (EI) m/z 334 (M+); 1H-NMR (CDCl3) δ 8.11 (1H, s), 7.43 (2H, d, J=8.3 Hz), 7.30 (2H, d, J=8.3 Hz), 3.11 (2H, t, J=6.6 Hz), 2.92 (2H, t, J=6.6 Hz), 2.81 (2H, q, J=7.5 Hz), 1.35 (3H, t, J=7.5 Hz).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. customPurification by preparative TLC (dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-703459a1f7584ef4a1443c136941a19c
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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