Potassium Carbonate → Methyl 4-[1-(dimethylamino)ethenyl]-3-methyl-2-thiophenecarboxylate

HRID 2392273Notes

Reaction equation

Br[C:2]1[C:3]([CH3:11])=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1.[C:12]([O-])([O-])=O.[K+].[K+].[CH3:18][N:19]1[C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22]C=N1>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>[CH3:18][N:19]([CH3:12])[C:23]([C:2]1[C:3]([CH3:11])=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1)=[CH2:22]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 4-bromo-3-methyl-2-thiophenecarboxylate (300 mg, 1.27 mmol) in dioxane/H2O (5 mL/1 mL) was added K2CO3 (525 mg, 3.80 mmol), tetrakistriphenylphosphine Pd(0) (15 mg, 0.01 mmol), and 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (345 mg, 1.7 mmol). The reaction mixture was heated to 70° C. in a sealed tube for 2 h. The reaction solution was concentrated under vacuum and purified on silica gel (hexanes/EtOAc, 9:1 to 4:1) to give the title compound (270 mg, 90%): LC-MS (ES) m/z 237 (M+H)+.

Workup

concentrationThe reaction solution was concentrated under vacuum
custompurified on silica gel (hexanes/EtOAc, 9:1 to 4:1)

Sources & evidence

ORD record: ord-1d51fb20d6dd42929580f2958c5d70c9
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273782B2

Reaction notes

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