Triethylamine → HCID 69514568, compound

HRID 858151Notes

Reaction equation

HRID 858151 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)=[CH:9][CH:8]=1)(=O)=O.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[CH3:22][N:21]1[CH:19]2[CH2:18][CH2:17][CH:16]1[CH2:15][CH:14]([S:13][C:10]1[CH:11]=[CH:12][C:7]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:8][CH:9]=1)[CH2:20]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 72415920HCID 72415920, compound

Product 1

HCID 69514568HCID 69514568, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4-[(8-methyl-8-azabicylo[3.2.1]oct-3-yl)thio]phenyl trifluoromethanesulfonate (0.4 g) and phenylboronic acid (0.25 g) in DMF (5 ml) were added triethylamine (0.58 ml) followed by dichlorobis(triphenylphosphine) palladium (II) (0.04 g). The solution was heated at 90° C. for 4 hours, cooled to room temperature and diluted with ethyl acetate. This was washed with saturated aqueous sodium hydrogen carbonate solution, then brine, dried (MgSO4), filtered and evaporated. Partial clean up was achieved using preparative LC-MS. The mixture was stirred with aqueous sodium hydroxide solution (0.5M) to hydrolyse residual triflate to the phenol. The product was extracted into ethyl acetate, still however contaminated with some of the phenol. The material was loaded onto a PE-AX column and eluted with methanol with the final clean up by preparative LC-MS to yield [1,1 ′-biphenyl]4-yl 8-methyl-8-azabicyclo[3.2. 1]oct-3-yl sulfide.

Workup

  1. temperaturecooled to room temperature
  2. washThis was washed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialbrine, dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. extractionThe product was extracted into ethyl acetate
  7. washeluted with methanol with the final clean up by preparative LC-MS

Sources & evidence

ORD record
ord-939b53c39bba41d2bdbdff6f50f7190e
Source dataset
uspto-grants-2006_12
Patent number
US07148236B2

Reaction notes

Loading…