Pyridine → HCID 16203635, compound

HRID 1078523Notes

Reaction equation

HRID 1078523 reaction equation
[N:1]([CH2:4][C@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[C:13]([F:30])[CH:12]=2)[CH2:6]1)=[N+]=[N-].N1C=CC=CC=1.[C:37](OC(=O)C)(=[O:39])[CH3:38]>C(OCC)(=O)C.[Pd]>[C:37]([NH:1][CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[C:13]([F:30])[CH:12]=2)[CH2:6]1)(=[O:39])[CH3:38]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86749742HCID 86749742, compound

Product 1

HCID 16203635HCID 16203635, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 14.92 g (35.5 mmol) of the azide 4 in 2000 mL of ethyl acetate was treated with 2 g of 10% palladium on carbon followed by hydrogenation at one atmosphere for 24 h. The flask was flushed with nitrogen, followed by sequential addition of 14.0 g (14.4 ml, 177.5 mmol) of pyridine and 9.1 g (8.4 mL, 88.8 mmol) of acetic anhydride. The mixture was stirred at ambient temperature for 72 h, followed by filtration through celite. The filtrate was extracted with water, 1N copper sulfate solution, dried and concentrated in vacuo to afford a tan solid. This material was purified by silica gel chromatography to afford 12.7 g (82%) of the product 5 as a powdery white solid, mp 153°-159° C.

Workup

  1. customThe flask was flushed with nitrogen
  2. filtrationfollowed by filtration through celite
  3. extractionThe filtrate was extracted with water, 1N copper sulfate solution
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto afford a tan solid
  7. customThis material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c66f42ce4a0343a08e56763a6b7d4caf
Source dataset
uspto-grants-1996_08
Patent number
US05547950

Reaction notes

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