Potassium Carbonate → HCID 67002903, compound

HRID 2362719Notes

Reaction equation

Cl[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]2[N:9]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:10]([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)=[CH:11][C:3]=12.[Br:26][C:27]1[CH:28]=[N:29][NH:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[Br:26][C:27]1[CH:28]=[N:29][N:30]([C:2]2[C:7]([Cl:8])=[CH:6][N:5]=[C:4]3[N:9]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:10]([C:12]4[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=4)=[CH:11][C:3]=23)[CH:31]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of Example 113E (0.194 g, 0.488 mmol) and 4-bromo-1H-pyrazole (0.115 g, 0.781 mmol) in 1-methyl-2-pyrrolidinone (0.8 mL) was treated with potassium carbonate (0.169 g, 1.22 mmol), and the reaction was heated at 150° C. for 2.5 hours. The reaction was cooled to ambient temperature, and partitioned between water and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by flash chromatography on a silica gel column, eluting with a gradient of 0% to 1% methanol in dichloromethane, to provide the title compound. MS ESI(+) m/z 509.0 [M+H]+.

Workup

temperatureThe reaction was cooled to ambient temperature
custompartitioned between water and ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe concentrate was purified by flash chromatography on a silica gel column
washeluting with a gradient of 0% to 1% methanol in dichloromethane

Sources & evidence

ORD record: ord-56e27a4facf147b6918cbb76f1107e48
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691810B2

Reaction notes

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