HCID 136340575, compound → HCID 136340576, compound

HRID 1522708Notes

Reaction equation

HRID 1522708 reaction equation
[N+:1]([C:4]1[CH:50]=[CH:49][C:7]([O:8][C:9]2[CH:10]=[C:11]([C:15]3[O:19][C:18]([C:20]4[CH:25]=[C:24]([OH:26])[C:23]([C:27]5[O:28][C:29]([C:32]6[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]7[CH:44]=[CH:43][C:42]([N+:45]([O-])=O)=[CH:41][CH:40]=7)[CH:33]=6)=[N:30][N:31]=5)=[CH:22][C:21]=4[OH:48])=[N:17][N:16]=3)[CH:12]=[CH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O>C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:10]=[C:11]([C:15]3[O:19][C:18]([C:20]4[CH:25]=[C:24]([OH:26])[C:23]([C:27]5[O:28][C:29]([C:32]6[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]7[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=7)[CH:33]=6)=[N:30][N:31]=5)=[CH:22][C:21]=4[OH:48])=[N:17][N:16]=3)[CH:12]=[CH:13][CH:14]=2)=[CH:49][CH:50]=1

Participants

4

Reactant 1

HCID 136340575HCID 136340575, compound

Product 1

HCID 136340576HCID 136340576, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.30 g of 2,5-bis(5-(3-(4-nitrophenoxy)phenyl)-1,3,4-oxadiazole-2-yl)benzene-1,4-diol prepared in Synthesis Example 15 was dissolved in 150 ml of THF, and 0.05 g of a catalyst having 5 wt % of palladium impregnated in activated carbon was added thereto. Gases generated in the solution by purging an argon (Ar) gas were removed to create a vacuum, followed by stirring for 18 hours while supplying H2 gas (approximately 2-3 atm) for inducing a reaction. After the reaction was completed, the reaction product was filtered with Celite powder to remove the catalyst, and performing silica gel column chromatography (developed with a solution having ethylacetate:n-hexane mixed in a ratio of 1:2) to yield 0.1 g of a product having Formula 39. 1H NMR (300 MHz, CDCl3) analytical results of the product were as follows:

Workup

  1. additionwas added
  2. customby purging an argon (Ar) gas
  3. customwere removed
  4. customa reaction
  5. filtrationthe reaction product was filtered with Celite powder
  6. customto remove the catalyst
  7. additionn-hexane mixed in a ratio of 1:2)

Sources & evidence

ORD record
ord-a95e5a909b62424ab573ab1aa6acf308
Source dataset
uspto-grants-2015_07
Patent number
US09077155B2

Reaction notes

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