Cesium carbonate → HCID 86674762, compound

HRID 927516Notes

Reaction equation

HRID 927516 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:17]1(B2OC(C)(C)C(C)(C)O2)[CH2:21][CH2:20][CH2:19][CH:18]=1>CN(C=O)C.O.C(Cl)Cl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:17]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=2)[CH2:21][CH2:20][CH2:19][CH:18]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 6085445-Bromopyridine-2-carboxylic acidHCID 154866112-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 86674762HCID 86674762, compoundYield 40.7%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

5-Bromo-pyridine-2-carboxylic acid (CAN 30766-11-1, 3.4 g, 17 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464-05-4, 530 mg, 0.65 mmol) and Cs2CO3 (6.3 g, 19 mmol) were added to a solution of 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAN 287944-10-9, 2.5 g, 13 mmol) in DMF (50 mL) and water (10 mL). The mixture was stirred at 150° C. overnight and concentrated in vacuo. Water (50 mL) was added and the mixture was extracted with ethyl acetate (3×40 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated to give the title compound (1.0 g, 31%); MS (EI): m/e=190.1 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionWater (50 mL) was added
  3. extractionthe mixture was extracted with ethyl acetate (3×40 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fbfcdf11744b40558905b888978638d4
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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