Potassium Carbonate → 5-(1-methyl-1H-pyrazol-5-yl)-3-thiophenecarboxylic acid

HRID 1967109Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=[O:8])[CH:6]=1.C([O-])([O-])=O.[K+].[K+].CC1(C)COB([C:23]2[N:27]([CH3:28])[N:26]=[CH:25][CH:24]=2)OC1>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>[CH3:28][N:27]1[C:23]([C:2]2[S:3][CH:4]=[C:5]([C:7]([OH:9])=[O:8])[CH:6]=2)=[CH:24][CH:25]=[N:26]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-bromo-4-thiophenecarboxylic acid (104 mg, 0.5 mmol) in dioxane/H2O (4:1, 10 mL) was added K2CO3 (271 mg, 1.99 mmol), tetrakistriphenylphosphine Pd(0) (28.7 mg, 0.025 mmol) and 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (97 mg, 0.5 mmol). The reaction mixture was heated to 80° C. in a sealed tube for 12 h and was then partitioned between 6N NaOH and DCM. The pH of the aqueous phase was adjusted to ˜3 with 3M HCl and washed several times with DCM. The combined organic fractions were dried (Na2SO4), concentrated under vacuum and used directly without further purification (104 mg, quant.): LC-MS (ES) m/z=209 (M+H)+.

Workup

customwas then partitioned between 6N NaOH and DCM
washwashed several times with DCM
dry with materialThe combined organic fractions were dried (Na2SO4)
concentrationconcentrated under vacuum
customused directly without further purification (104 mg, quant.)

Sources & evidence

ORD record: ord-1723f1ce9dd84340908910728ec4574c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420690B2

Reaction notes

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