Potassium Carbonate → HCID 59591442, compound

HRID 1963014Notes

Reaction equation

Br[CH2:2][C:3]1[S:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:4]=1.[F:15][C:16]1[C:23]([OH:24])=[CH:22][CH:21]=[C:20]([F:25])[C:17]=1[C:18]#[N:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[N:4]=[C:3]([CH2:2][O:24][C:23]3[C:16]([F:15])=[C:17]([C:20]([F:25])=[CH:21][CH:22]=3)[C:18]#[N:19])[S:7][N:6]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-bromomethyl-3-(4-chlorophenyl)-[1,2,4]thiadiazole (0.24 g, 0.82 mmol) in DMF (7 ml) was added 2,6-difluoro-3-hydroxybenzonitrile (0.12 g, 0.74 mmol) and potassium carbonate (0.39 g, 2.90 mmol). The reaction mixture was stirred at 25° C. for 2 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated to dryness under vacuum, added 50 ml water and extracted with ethyl acetate (3×40 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified over silica gel (100-200 M, 15% EtOAc-Hexane) to get the desired product (0.30 g, 73%).

Workup

customAfter the completion of the reaction (TLC monitoring)
customthe reaction mixture was evaporated to dryness under vacuum
additionadded 50 ml water
extractionextracted with ethyl acetate (3×40 ml)
dry with materialThe combined organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
customThe crude residue was purified over silica gel (100-200 M, 15% EtOAc-Hexane)

Sources & evidence

ORD record: ord-a254dd89ce7c42c28112e4c5f3cfa0b1
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415383B2

Reaction notes

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