Methanol → 3-[5-(4-Cyano-phenyl)-[1,3,4]thiadiazol-2-ylmethyl]-benzoic acid methyl ester

HRID 1468169Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][C:6]1[S: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.C1[CH2:26][O:25][CH2:24]C1.C1CCN2C(=NCCC2)CC1.C[OH:39]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][O:25][C:26](=[O:39])[C:2]1[CH:21]=[CH:20][CH:19]=[C:4]([CH2:5][C:6]2[S: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

Dissolve 4-[5-(3-iodo-benzyl)-[1,3,4]thiadiazol-2-yl]-benzonitrile (0.34 g, 0.75 mmol) into 8 mL of a 1:1 mixture of THF:MeOH in a microwave pressure tube. Add molybedinum hexacarbonyl (0.25 g, 0.95 mmol) and DBU (0.32 mL, 2.10 mmol) causing the solution to darken. Add palladium acetate (0.03 g, 0.11 mmol), seal the tube and heat at 100° C. in a microwave reactor for 10 min. Concentrate the mixture onto silica gel and purify by flash silica gel chromatography to provide (0.150 g, 60% yield of 3-[5-(4-cyano-phenyl)-[1,3,4]thiadiazol-2-ylmethyl]-benzoic acid methyl ester as a solid.

Workup

concentrationConcentrate the mixture onto silica gel
custompurify by flash silica gel chromatography

Sources & evidence

ORD record: ord-56c752b49e2f4a9399271e654b3702e9
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000154B2

Reaction notes

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