HCID 25254645, compound → HCID 135878207, compound

HRID 2167328Notes

Reaction equation

HRID 2167328 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.C1COCC1.[Pd]>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([C:17]2[N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[O:19][N:18]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 1

HCID 25254645HCID 25254645, compound

Product 1

HCID 135878207HCID 135878207, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(4-(Benzyloxy)phenyl)-3-(4-methoxyphenyl)-1,2,4-oxadiazole (50 mg, 139 μmol) and 10% Pd/C (1 mg, 10 μmol) were suspended in methanol (3.0 mL) and THF (3.0 mL). The solution was stirred in a round bottom flask fitted with a condenser and septa and placed under H2 at 55° C. for 95 hours. The solution was filtered through Celite and the solvent was removed under reduced pressure and then purified by silica gel column chromatography (EtOAc/Hex 1:2) to give the product (3 mg, 9%) as a white solid. 1H NMR (500 MHz, CDCL3) δ(ppm): 3.88 (3H, s), 5.55 (1H, s), 6.98 (2H, d, J=9.0 Hz), 7.01 (2H, d, J=8.4 Hz), 8.01 (2H, d, J=9.0 Hz), 8.12 (2H, d, J=8.2 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 55.6 (CH3), 114.4 (CH), 116.3 (CH), 117.4, 119.7, 129.3 (CH), 130.6 (CH), 159.6, 162.1, 168.7, 175.4. MS (FAB+): 269 (MH+). HRMS for C15H12N2O3 (MH+): calculated: 269.0926; found 269.0929.

Workup

  1. customfitted with a condenser
  2. filtrationThe solution was filtered through Celite
  3. customthe solvent was removed under reduced pressure
  4. custompurified by silica gel column chromatography (EtOAc/Hex 1:2)

Sources & evidence

ORD record
ord-799942461a124d56b614c4f3d2d52656
Source dataset
uspto-grants-2015_06
Patent number
US09045442B2

Reaction notes

Loading…