Ethanol → HCID 19008893, compound

HRID 1742429Notes

Reaction equation

HRID 1742429 reaction equation
C(O[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[N:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[N:21]=[C:20]1[CH2:28][CH2:29][CH2:30][CH3:31])C1C=CC=CC=1.CC[OH:34]>[Pd]>[CH2:28]([C:20]1[N:19]([C:10]2[CH:9]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][C:14]([OH:34])=[CH:15]3)[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[N:21]=1)[CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 702Ethanol2×HCID 19008931HCID 19008931, compound

Product 1

HCID 19008893HCID 19008893, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 3-(benzyloxy-naphthalen-1-yl)-2-butyl-3H-imidazo[4,5-b]-pyridine (1500 g) in EtOH (75 mL) was added to a mixture of Pd/C (3.56 g) in EtOH (50 mL). The mixture was hydrogenated on a paar shaker at 50 psi for 72 hours. The reaction mixture was filtered through celite and concentrated in vacuo to give 1.13 grams of an amorphous solid. 1H NMR (250 MHz, CDCl3): d 8.48 (d, 1 H), 8.24 (d, 1 H), 7.52 (m), 7.37 (dd, 1 H), 7.26 (d, 2 H), 6.68 (dd, 2 H), 6.60 (s, 1 H), 2.67 (t, 2 H), 170 (m, 2 H), 1.23 (m, 2 H), 0.78 (t, 3 H).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74310b18dcb742e7b8f4caa5c2044e93
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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