HCID 21875565, compound → HCID 21875554, compound

HRID 1454609Notes

Reaction equation

HRID 1454609 reaction equation
[C:1]([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]3=[N:19][CH:20]=[C:21]([N+:24]([O-])=O)[C:22]([CH3:23])=[C:17]3[N:16]=[C:15]2[CH2:27][CH3:28])=[CH:10][CH:9]=1)(=[O:4])[CH2:2][CH3:3]>CO.[Pd]>[C:1]([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]3=[N:19][CH:20]=[C:21]([NH2:24])[C:22]([CH3:23])=[C:17]3[N:16]=[C:15]2[CH2:27][CH3:28])=[CH:10][CH:9]=1)(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 21875565HCID 21875565, compound

Product 1

HCID 21875554HCID 21875554, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2-[4-(2-ethyl-7-methyl-6-nitro-3H-imidazo[4,5-b]pyridin-3-yl)phenyl]ethyl propionate (step 3, 2.5 g, 6.6 mmol), 10% Pd—C (250 mg, 0.23 mmol) in methanol (100 mL) was stirred under hydrogen atmosphere for 2 h. The suspension was filtered through a pad of Celite, and the filtrate was concentrated to afford 2.4 g (99%) of the title compound as a brown oil: 1H-NMR (CDCl3) δ 7.82 (1H, s), 7.41 (2H, d, J=8.2 Hz), 7.32 (2H, d, J=8.4 Hz), 4.35 (2H, t, J=7.0 Hz), 3.51 (2H, br.s), 3.03 (2H, t, J=7.0 Hz), 2.82 (2H, q, J=7.5 Hz), 2.53 (3H, s), 2.35 (2H, q, J=7.5 Hz), 1.29 (3H, t, J=7.5 Hz), 1.44 (3H, t, J=7.5 Hz).

Workup

  1. filtrationThe suspension was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6371baee88bd4551acfb4cbd6d8639b6
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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