Binap, (A+-)- → HCID 86645834, compound

HRID 1253702Notes

Reaction equation

HRID 1253702 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Br[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=1.CC([O-])(C)C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:26][C:25]([F:28])([F:27])[C:22]1[CH:23]=[CH:24][C:19]([N:8]2[CH2:7][CH2:6][C:5]3([CH2:1][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:4]3)[CH2:10][CH2:9]2)=[N:20][CH:21]=1

Participants

7

Reactant 4

HCID 634876Binap, (A+-)-HCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 23676156Sodium t-butoxideHCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

Product 1

HCID 86645834HCID 86645834, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (2.5 mmol, 1.0 eq.) and 2-bromo-5-(trifluoromethyl)pyridine (2.5 mmol, 1.0 eq.) and tBuONa (7.5 mmol, 3.0 eq.) in toluene (12 ml) was degassed with argon for 10 min. BINAP (0.15 mmol, 0.06 eq.) and Pd(OAc)2 (0.05 mmol, 0.02 eq.) were added and the reaction mixture obtained was heated under reflux for 14 h. The reaction mixture was filtered over Celite and the filtrate was concentrated in vacuo in order to obtain the crude product, which was purified by column chromatography (silica gel, 22-25% ethyl acetate in hexane), in order to obtain the desired product. Yield: 40%

Workup

  1. customwas degassed with argon for 10 min
  2. customthe reaction mixture obtained
  3. temperaturewas heated
  4. temperatureunder reflux for 14 h
  5. filtrationThe reaction mixture was filtered over Celite
  6. concentrationthe filtrate was concentrated in vacuo in order
  7. customto obtain the crude product, which
  8. customwas purified by column chromatography (silica gel, 22-25% ethyl acetate in hexane), in order

Sources & evidence

ORD record
ord-e07fd31bb4484ffa8d91bb9c2ac6b782
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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