Hydrochloric Acid → HCID 57826592, compound

HRID 1961024Notes

Reaction equation

HRID 1961024 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([CH3:15])[C:6]=1[C:7]1[CH:8]=[C:9]([C:12]([OH:14])=[O:13])[S:10][CH:11]=1.[C:16]([O-])([O-])=O.[K+].[K+].CC1(C)COB([C:29]2N(C)N=[CH:31][CH:30]=2)OC1.Cl.O1[CH2:42][CH2:41]OCC1.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>[CH3:15][N:5]1[C:6]([C:7]2[CH:8]=[C:9]([C:12]([OH:14])=[O:13])[S:10][CH:11]=2)=[C:2]([C:29]2[CH:30]=[CH:31][CH:42]=[CH:41][CH:16]=2)[CH:3]=[N:4]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 218864351,4-Dioxane--water (1/1)HCID 441194445-(5,5-Dimethyl-1,3,2-dioxaborinan-2-YL)-1-methyl-1H-pyrazole2×HCID 57826813HCID 57826813, compound

Product 1

HCID 57826592HCID 57826592, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst2×

Procedure

To a solution of 4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid (688 mg, 2.41 mmol) in dioxane/H2O (5:1, 12 mL) was added K2CO3 (1.3 g, 9.6 mmol), tetrakistriphenylphosphine Pd(0) (139 mg, 0.120 mmol), and 5-(5,5-dimethyl-1,3,2-dioxaborinane-2-yl)-1-methyl-1H-pyrazole (293 mg, 2.41 mmol). The reaction mixture was heated to 80° C. in a sealed tube for 2 h where additional tetrakistriphenylphosphine Pd(0) (139 mg, 0.120 mmol) and 5-(5,5-dimethyl-1,3,2-dioxaborinane-2-yl)-1-methyl-1H-pyrazole (293 mg, 2.41 mmol) were added. After 12 h, the solution was poured onto H2O and the pH was adjusted to ˜4 with aqueous HCl. The aqueous phase was extracted several times with DCM and the combined organic fractions were dried (Na2SO4) and concentrated affording the title compound white was used directly without further purification: LC-MS (ES) m/z=284 (M+H)+.

Workup

  1. additionwere added
  2. additionthe solution was poured onto H2O
  3. extractionThe aqueous phase was extracted several times with DCM
  4. dry with materialthe combined organic fractions were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1f32ab62172d4c7884583a875eba73e8
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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