Triphenylarsine → HCID 69524719, compound

HRID 858149Notes

Reaction equation

HRID 858149 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH:14]2[CH2:20][CH:19]3[N:21]([CH3:22])[CH:16]([CH2:17][CH2:18]3)[CH2:15]2)=[C:9]([Cl:23])[CH:8]=1)(=O)=O.[Cl-].[Li+].C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Sn](CCCC)(CCCC)[C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1)CCC.[OH-].[Na+]>CN1CCCC1=O.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]>[Cl:23][C:9]1[CH:8]=[C:7]([C:52]2[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=2)[CH:12]=[CH:11][C:10]=1[S:13][CH:14]1[CH2:20][CH:19]2[N:21]([CH3:22])[CH:16]([CH2:17][CH2:18]2)[CH2:15]1

Participants

8

Reactant 5

HCID 11773TriphenylarsineHCID 14798Sodium HydroxideHCID 433294Lithium ChlorideHCID 34838483-(Tributylstannyl)pyridineHCID 87869973HCID 87869973, compound

Product 1

HCID 69524719HCID 69524719, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-chloro-4-[(8-methyl-8-azabicylo[3.2.1]oct-3-yl)thio]phenyl trifluoromethanesulfonate (215 mg), lithium chloride (70 mg), triphenylarsine 32 mg) and tris(dibenzylideneacetone)-dipalladium (0) (20 mg) was stirred in N-methylpyrrolidinone (10 ml) under nitrogen for 5 minutes. To this was added 3-tributylstannylpyridine (200 mg) and the solution heated to 100° C. for 2 hours. The solution was cooled to room temperature and aqueous sodium hydroxide (10%) added to quench the reaction. The mixture was extracted three times with dichloromethane, the combined organics dried (MgSO4), filtered and evaporated to dryness. The material was purified on an SCX cartridge eluting sequentially with methanol and 2M ammonia in methanol, followed by preparative LC-MS yielding 3-{[2-chloro-4-(3-pyridinyl)phenyl]thio}-8-methyl-8-azabicylo[3.2.1]octane (54 mg)

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture was extracted three times with dichloromethane
  5. dry with materialthe combined organics dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe material was purified on an SCX cartridge
  9. washeluting sequentially with methanol and 2M ammonia in methanol

Sources & evidence

ORD record
ord-e4df7f99f7ee4072b49bf14a618e924a
Source dataset
uspto-grants-2006_12
Patent number
US07148236B2

Reaction notes

Loading…