Potassium Acetate → 5-Methoxy-2-(3-methyl-1,2,4-thiadiazol-5-yl)-benzaldehyde

HRID 1966704Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1B(O)O)=[O:2].Cl[C:15]1[S:19][N:18]=[C:17]([CH3:20])[N:16]=1.C([O-])(=O)C.[K+]>O1CCOCC1.O>[CH3:10][O:9][C:7]1[CH:6]=[CH:5][C:4]([C:15]2[S:19][N:18]=[C:17]([CH3:20])[N:16]=2)=[C:3]([CH:8]=1)[CH:1]=[O:2]

Participants

Conditions

Temperature: 100 °C

Procedure

In a microwave vial are combined 2-formyl-4-methoxyphenylboronic acid (432 mg, 2.40 mmol), 5-chloro-3-methyl-1,2,4-thiadiazole (270 mg, 2.00 mmol), potassium acetate (390 mg, 4.00 mmol), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)-dichloropalladium(II) (283 mg, 0.40 mmol) in 1,4-dioxane (6 mL) and water (0.50 mL). The reaction vial is sealed and stirred at 100° C. for 20 hours. The reaction mixture is cooled to ambient temperature and poured into water and extracted with EtOAc (3×). The combined organics are dried (MgSO4), filtered and concentrated. Purification via flash chromatography (12 g silica gel, 5-40% EtOAc/heptane) affords 5-methoxy-2-(3-methyl-1,2,4-thiadiazol-5-yl)-benzaldehyde which is used without further purification.

Workup

customThe reaction
customvial is sealed
temperatureThe reaction mixture is cooled to ambient temperature
extractionextracted with EtOAc (3×)
dry with materialThe combined organics are dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customPurification via flash chromatography (12 g silica gel, 5-40% EtOAc/heptane)

Sources & evidence

ORD record: ord-461b4271655c4ae2b032fd9c76054290
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420655B2

Reaction notes

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