Potassium Carbonate → HCID 57826434, compound

HRID 1961017Notes

Reaction equation

HRID 1961017 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([NH:10][C@@H:11]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:30])[F:29])[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:9])[S:5][C:6]=1[Cl:7].C([O-])([O-])=O.[K+].[K+].CC1(C)COB([C:45]2[N:49]([CH3:50])[N:48]=[CH:47][CH:46]=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>[Cl:7][C:6]1[S:5][C:4]([C:8]([NH:10][C@@H:11]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:30])[F:29])[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:9])=[CH:3][C:2]=1[C:45]1[N:49]([CH3:50])[N:48]=[CH:47][CH:46]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 441194445-(5,5-Dimethyl-1,3,2-dioxaborinan-2-YL)-1-methyl-1H-pyrazole2×HCID 57826803HCID 57826803, compound

Product 1

HCID 57826434HCID 57826434, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 1,1-dimethylethyl {(2S)-2-{[(4-bromo-5-chloro-2-thienyl)carbonyl]amino}-3-[2-(trifluoromethyl)phenyl]propyl}carbamate (750 mg, 1.38 mmol) in dioxane/H2O (5:1, 6 mL) was added K2CO3 (762 mg, 5.52 mmol), tetrakistriphenylphosphine Pd(0) (80 mg, 69 umol), and 5-(5,5-dimethyl-1,3,2-dioxaborinane-2-yl)-1-methyl-1H-pyrazole (373 mg, 1.8 mmol). The reaction mixture was heated to 80° C. in a sealed tube for 2 h where additional tetrakistriphenylphosphine Pd(0) (80 mg, 69 umol) and 5-(5,5-dimethyl-1,3,2-dioxaborinane-2-yl)-1-methyl-1H-pyrazole (373 mg, 1.8 mmol) were added. After 12 h, the solution was poured onto H2O (100 mL) and extracted with DCM. The organics were dried (Na2SO4), concentrated under vacuum, and purified on silica gel (hexanes/EtOAc, 1:1) to give the title compound (194 mg, 26%) as a white solid: LC-MS (ES) m/z=544.

Workup

  1. additionwere added
  2. additionthe solution was poured onto H2O (100 mL)
  3. extractionextracted with DCM
  4. dry with materialThe organics were dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. custompurified on silica gel (hexanes/EtOAc, 1:1)

Sources & evidence

ORD record
ord-72c8de6bc56d49dda44d31c3434683e6
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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