Binap, (A+-)- → HCID 12016227, compound

HRID 2305404Notes

Reaction equation

HRID 2305404 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:7]=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][C@@H:28]2[CH2:30][C@H:25]1[CH2:26][NH:27]2)=[O:23])([CH3:20])([CH3:19])[CH3:18].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+]>[Cl-].[Na+].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].C1(C)C=CC=CC=1>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:7]=[C:2]([N:27]3[CH2:26][C@@H:25]4[CH2:30][C@H:28]3[CH2:29][N:24]4[C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])[CH:3]=[N:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 634876Binap, (A+-)-HCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 120162263-Bromo-5-(4-methoxyphenoxy)pyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 12016227HCID 12016227, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 5234Sodium ChlorideSolvent

Procedure

In a sealed pressure tube under a argon atmosphere, 3-bromo-5-(4-methoxyphenoxy)pyridine (2.37 g, 1.20 mmol), (1S,4S)-N-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane (0.21 g, 1.00 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.02 g, 0.02 mmol, 2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.025 g, 0.04 mmol), sodium tert-butoxide (0.20 g, 2.0 mmol) and toluene (12 mL) was stirred at 80° C. for 24 h. The reaction mixture was dissolved in saturated aqueous sodium chloride solution (20 mL) and then extracted with diethyl ether (3×30 mL). The combined diethyl ether extracts were washed with saturated aqueous sodium chloride solution (20 mL), dried (Na2SO4), filtered and concentrated to a brown oil (0.37 g, 93%). The material was used without further purification.

Workup

  1. extractionextracted with diethyl ether (3×30 mL)
  2. washThe combined diethyl ether extracts were washed with saturated aqueous sodium chloride solution (20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a brown oil (0.37 g, 93%)
  6. customThe material was used without further purification

Sources & evidence

ORD record
ord-94728c8d75d0464e9882c8625bca5ffa
Source dataset
uspto-grants-2002_08
Patent number
US06440970B1

Reaction notes

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