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Potassium Carbonate → 5-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid

HRID 1845372
Notes
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Reaction equation

HRID 1845372 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=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:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=2)=[CH:24][CH:25]=[N:26]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3491155-Bromothiophene-2-carboxylic acidHCID 441194445-(5,5-Dimethyl-1,3,2-dioxaborinan-2-YL)-1-methyl-1H-pyrazole

Product 1

HCID 586573295-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compound
Catalyst
HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-2-thiophenecarboxylic acid (100 mg, 0.48 mmol) in dioxane/H2O (5:1, 6 mL) was added K2CO3 (267 mg, 1.93 mmol), tetrakistriphenylphosphine Pd(0) (28 mg, 24 umol) and 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (94 mg, 0.48 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 (−100 mg, quant.): LC-MS (ES) m/z=209 (M+H)+.

Workup

  1. customwas then partitioned between 6N NaOH and DCM
  2. washwashed several times with DCM
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. concentrationconcentrated under vacuum
  5. customused directly without further purification (−100 mg, quant.)

Sources & evidence

ORD record
ord-ae5548fc422540feb3f43e0aebfd901c
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946278B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes