Cesium carbonate → Tert-butyl 4-(2-methylquinolin-5-yl)piperazine-1-carboxylate

HRID 15820

Reaction equation

HRID 15820 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11]([CH3:17])=[N:12]2)(=O)=O.[C:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=C(C3C4C(=CC=CC=4)C=CC=3)C3C(C=2)=CC=CC=3)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:17][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][CH:15]=[CH:16][C:7]=2[N:30]2[CH2:29][CH2:28][N:27]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:32][CH2:31]2)[N:12]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 18630801Bis(diphenylphosphino)-1,1'-binaphthylHCID 498518992-Methylquinolin-5-yl trifluoromethanesulfonate

Product 1

HCID 49851900Tert-butyl 4-(2-methylquinolin-5-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 2-methyl-5-quinolinyl trifluoromethanesulfonate (lwt, 1 eq) in toluene (7 vol) was degassed under reduced pressure then flushed with nitrogen. To the mixture were added N-Boc-piperazine (1.05 eq), milled cesium carbonate (1.5 eq), (+/−)-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 0.15 eq) and palladium acetate (0.05 eq). The resulting mixture was stirred at 95° C. for 16 hours. The solution was cooled and concentrated to approx. 4 vol and 10 vol of cyclohexane were added giving a suspension. The suspension was stirred for 30 minutes and filtered over a pad of Silica Gel (approx 2.5 vol). The filtrate was washed with 10 vol of water and concentrated under reduced pressure to give the title compound as a brown solid, which was carried through directly to the next stage.

Workup

  1. customthen flushed with nitrogen
  2. temperatureThe solution was cooled
  3. concentrationconcentrated
  4. additionwere added
  5. customgiving a suspension
  6. stirringThe suspension was stirred for 30 minutes
  7. filtrationfiltered over a pad of Silica Gel (approx 2.5 vol)
  8. washThe filtrate was washed with 10 vol of water
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-139e0c730c15469ca499aa8643504939
Source dataset
uspto-grants-2010_06
Patent number
US07732600B2

Linked notes

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