Potassium Carbonate → HCID 59427899, compound

HRID 502761Notes

Reaction equation

HRID 502761 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([CH3:10])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].B1C2CCCC1CCC2.Br[C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[NH2:24].C(=O)([O-])[O-].[K+].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)Cl.O.CN(C=O)C>[CH3:10][N:7]1[CH2:8][CH2:9][N:4]([CH2:1][CH2:2][CH2:3][C:21]2[CH:22]=[C:23]([NH2:24])[CH:25]=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:27]=2)[CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 27358803-Bromo-5-(trifluoromethyl)anilineHCID 12654562HCID 12654562, compound

Product 1

HCID 59427899HCID 59427899, compound

Reagents, catalysts & solvents 3

HCID 178478482HCID 178478482, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-allyl-4-methylpiperazine (2.12 g, 14.0 mmol) and 9-BBN (0.5 M in THF, 1.7 g, 28 mL, 14.0 mmol) was heated at reflux for 3 h and then cooled to RT. The solution was added to a mixture of 3-bromo-5-(trifluoromethyl)aniline (3.0 o g, 12.5 mmol), potassium carbonate (8.64 g, 62.5 mmol), PdCl2(PPh3)2—CH2Cl2 adduct (0.457 g, 0.6 mmol), DMF (30 mL) and water (2 mL). The mixtre was heated to 75° C. for 24. The mixture was concentrated, triturated with dichloromethane, and filtered. The filtrate was concentrated and the residue was purified via column chromatography on silica gel (gradient elution with 0-20% methanol-dichloromethane) to afford 3-(3-(4-methylpiperazin-1-yl)propyl)-5-(trifluoromethyl)benzenamine as a brown oil. MS m/z=302 [M+H]+. Calc'd for C15H22F3N3: 301.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureThe mixtre was heated to 75° C. for 24
  3. concentrationThe mixture was concentrated
  4. customtriturated with dichloromethane
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified via column chromatography on silica gel (gradient elution with 0-20% methanol-dichloromethane)

Sources & evidence

ORD record
ord-d645592eada24a2c9b2a3310a9ce7810
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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