Potassium Carbonate → HCID 11394127, compound

HRID 1798947Notes

Reaction equation

HRID 1798947 reaction equation
B1C2CCCC1CCC2.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20](=[CH2:23])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].Br[C:25]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][N:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][C:25]2[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][N:26]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 789669-Borabicyclo(3.3.1)nonaneHCID 27568081-Boc-4-Methylenepiperidine

Product 1

HCID 11394127HCID 11394127, compound

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 9-BBN (0.5 N in THF, 100 mL) was added 4-methylenepiperidine-1-carboxylic acid tert-butyl ester (1.23 g, 1.5 mmol) the reaction mixture was stirred at reflux for 1 h. The reaction mixture was cooled to RT and added via a syringe to a solution of 2,5-dibromopyridine (11.3 g, 47.5 mmol) and Pd(dppf)Cl2 dichloromethane (1.23 g, 1.5 mmol) dissolved in DMF (100 mL) and water (9.9 mL) and K2CO3 (8.29 g). This mixture was heated at 60° C. for 3 hours. The DMF was the removed in vacuo. Addition of Ethylactetate/heptane afforded only some crystallisation. Therefore was the crude mixture evaporated once more to an oil. Further purification on a CombiFlash with Ethyl actetate/heptane (9:1) as eluent afforded 4-(5-bromopyridin-2-ylmethyl)piperidine-1-carboxylic acid tert-butyl ester as a brown oil. Yield: 8 g, (45%).

Workup

  1. temperatureat reflux for 1 h
  2. temperatureThis mixture was heated at 60° C. for 3 hours
  3. customremoved in vacuo
  4. additionAddition of Ethylactetate/heptane
  5. customafforded only
  6. customsome crystallisation
  7. customevaporated once more to an oil
  8. customFurther purification on a CombiFlash with Ethyl actetate/heptane (9:1) as eluent

Sources & evidence

ORD record
ord-82a9c97784864293ae1f49c78e321240
Source dataset
uspto-grants-2013_01
Patent number
US08344001B2

Reaction notes

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