HCID 23156127, compound → HCID 69435197, compound

HRID 1890628Notes

Reaction equation

HRID 1890628 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21](N=[N+]=[N-])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]>C(O)C.[C].[Pd]>[CH2:21]([C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:13]2[C:6]3=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]3[N:4]=[C:3]2[CH2:1][CH3:2])=[CH:20][CH:19]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 23156127HCID 23156127, compound

Product 1

HCID 69435197HCID 69435197, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

[4-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)phenyl]phenylmethylazide (0.580 g, 1.46 mmol) obtained in Step 1 was dissolved in ethanol (30 mL), and the flask was filled with argon. 10% Palladium-carbon (50% wet, 0.311 g) was added to the solution, followed by stirring for 6 hours under hydrogen atmosphere. The unsoluble material was filtered out through Celite, and washed with ethanol. The filtrate was combined and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether-hexane to obtain Compound 4 (0.510 g, yield 94%).

Workup

  1. additionthe flask was filled with argon
  2. filtrationThe unsoluble material was filtered out through Celite
  3. washwashed with ethanol
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-ddd2578dc6214bcb9e4e887ad9230f39
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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