1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-[5-(4-Cyano-phenyl)[1,3,4]oxadiazol-2-ylmethyl]-benzoic acid methyl ester

HRID 1468166Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][C:6]1[O:10][C:9]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)=[N:8][N:7]=1.C1CCN2C(=NCCC2)CC1.[O:33]1[CH2:37]CC[CH2:34]1.C[OH:39]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:34][O:33][C:37](=[O:39])[C:2]1[CH:21]=[CH:20][CH:19]=[C:4]([CH2:5][C:6]2[O:10][C:9]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)=[N:8][N:7]=2)[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Add molybedinum hexacarbonyl (0.07 g, 0.26 mmol) to 4-[5-(3-iodo-benzyl)-[1,3,4]oxadiazol-2-yl]-benzonitrile (0.10 g (0.26 mmol) in 2 mL of a 1:1 mixture of tetrahydrofuran MeOH in a microwave pressure tube. Add DBU (0.11 mL, 0.74 mmol) causing the solution to darken. Add palladium acetate (0.006 g, 0.030 mmol) to the mixture, seal the tube and heat at 100° C. in a microwave reactor for 10 minutes. Cool the mixture to room temperature and purify by flash silica gel chromatography to give 0.04 g 48% yield of 3-[5-(4-cyano-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-benzoic acid methyl ester a solid.

Workup

temperatureCool the mixture to room temperature
custompurify by flash silica gel chromatography

Sources & evidence

ORD record: ord-3e5139b5202d40de8c0a05c38e12cdf4
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000154B2

Reaction notes

Loading…