3,5-Dibromopyridine → HCID 67606621, compound

HRID 1774986Notes

Reaction equation

HRID 1774986 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[C:9]([NH:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:8][C:6]1[CH:7]=[C:2]([N:20]2[CH2:19][CH2:18][CH:17]([NH:16][C:9](=[O:10])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:22][CH2:21]2)[CH:3]=[N:4][CH:5]=1

Participants

7

Reactant 4

HCID 693693,5-DibromopyridineHCID 634876Binap, (A+-)-HCID 7238334-(N-Boc-amino)piperidineHCID 23676156Sodium t-butoxide

Product 1

HCID 67606621HCID 67606621, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of 3,5-dibromopyridine (0.400 g, 1.69 mmol), 4-(N-Boc-amino)-piperidine (0.238 g, 1.19 mmol), Tris(dibenzylideneacetone)dipalladium(0) (54 mg, 0.059 mmol), rac-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (73.9 mg, 0.119 mmol), and Sodium-tert-butoxide (114 mg, 1.19 mmol) in Toluene (16.9 mL) was heated at 85° C. for 18 h. The reaction was filtered thru celite then rinsed with EtOAc. The crude product was purified by Isco (EtOAc/Hep eluted at 40%) to give tert-butyl 1-(5-bromopyridin-3-yl)piperidin-4-ylcarbamate (320 mg, 75.6% yield). ESI MS m/z=357.1 (M+1).

Workup

  1. filtrationThe reaction was filtered thru celite
  2. washthen rinsed with EtOAc
  3. customThe crude product was purified by Isco (EtOAc/Hep eluted at 40%)

Sources & evidence

ORD record
ord-db0154593d3541209a0e5b17f9a6064d
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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