Sodium Carbonate → HCID 57992296, compound

HRID 1921236Notes

Reaction equation

HRID 1921236 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:15]1[CH:24]=[C:23]2[C:18]([CH2:19][CH2:20][N:21](C(=O)C(F)(F)F)[CH2:22]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:15]2[CH:24]=[C:23]3[C:18]([CH2:19][CH2:20][NH:21][CH2:22]3)=[CH:17][CH:16]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 109688311-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

Product 1

HCID 57992296HCID 57992296, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

4.63 g 4-(Trifluormethyl)phenylboronic acid was dissolved in 15 ml ethanol and added to a mixture of 5.0 g 1-(7-bromo-3,4-dihydro-1H-isoquinolin-2-yl)-2,2,2-trifluoro-ethanone in 150 ml toluene and 54 ml of a 2 molar sodium carbonate solution. The reaction mixture was degassed then 940 mg tetrakis(triphenylphosphine)palladium(0) was added and the mixture heated under reflux for two hours. The cooled reaction mixture was evaporated, the resulting residue was dissolved in 150 ml ethyl acetate and washed with 50 ml water and brine. The organic layer was dried over MgSO4 and the solvent removed in vacuo. The resulting crude material was purified by reversed phase HPLC to obtain 2.0 g 7-(4-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-isoquinoline as its trifluoroacetate salt.

Workup

  1. customThe reaction mixture was degassed
  2. addition940 mg tetrakis(triphenylphosphine)palladium(0) was added
  3. temperaturethe mixture heated
  4. temperatureunder reflux for two hours
  5. customThe cooled reaction mixture
  6. customwas evaporated
  7. dissolutionthe resulting residue was dissolved in 150 ml ethyl acetate
  8. washwashed with 50 ml water and brine
  9. dry with materialThe organic layer was dried over MgSO4
  10. customthe solvent removed in vacuo
  11. customThe resulting crude material was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-cdfb4ae9b8df4ddb8fb72c4a66e9001f
Source dataset
uspto-grants-2012_05
Patent number
US08173674B2

Reaction notes

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