Potassium Carbonate → HCID 57826679, compound

HRID 1845433Notes

Reaction equation

HRID 1845433 reaction equation
Br[C:2]1[C:3]([O:11][CH3:12])=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1.CC1(C)COB([C:20]2[N:24]([CH3:25])[N:23]=[CH:22][CH:21]=2)OC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:11][C:3]1[C:2]([C:20]2[N:24]([CH3:25])[N:23]=[CH:22][CH:21]=2)=[CH:6][S:5][C:4]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2736824Methyl 4-bromo-3-methoxythiophene-2-carboxylateHCID 441194445-(5,5-Dimethyl-1,3,2-dioxaborinan-2-YL)-1-methyl-1H-pyrazole

Product 1

HCID 57826679HCID 57826679, compoundYield 852.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-bromo-3-(methyloxy)-2-thiophenecarboxylate (250 mg, 0.10 mmol) [prepared according to Corral, C.; El-Ashmawy, M. B.; Lissavetzky, J.; Basilio, A.; Giraldez, A.; Eur. J. Med. Chem. Chim. Ther. 22; 1987; 251-254.], 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (250 mg, 1.20 mmol), Pd(PPh3)4 (58 mg, 49.8 μmol) and K2CO3 (550 mg, 3.98 mmol) in dioxane (5 mL) and H2O (1 mL) were combined in a sealed tube. After 12 h at 80° C., the reaction contents were partitioned between H2O/DCM. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (silica, 0.5% MeOH in DCM) affording the title compound (215 mg, 86%) as a brown residue: LCMS (ES) m/z=253 (M+H)+.

Workup

  1. customthe reaction contents
  2. customwere partitioned between H2O/DCM
  3. washThe aqueous phase was washed several times with DCM
  4. dry with materialthe combined organic fractions were dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified via column chromatography (silica, 0.5% MeOH in DCM)

Sources & evidence

ORD record
ord-79e1d0aad8324d618e30580420014468
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

Loading…