1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 24947036, compound

HRID 1803573Notes

Reaction equation

HRID 1803573 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[C:5]2[Cl:13].[F:14][C:15]([F:29])([F:28])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:17]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>CC(N(C)C)=O.CCOC(C)=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:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([N:25]3[CH2:24][CH2:23][N:22]([C:18]4[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([F:28])([F:29])[F:14])[CH:17]=4)[CH2:27][CH2:26]3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

8

Reactant 4

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 24947036HCID 24947036, compoundYield 6.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.578 mmol), 1-(α,α,α-trifluoro-m-tolyl)piperazine (0.12 mL, 0.639 mmol), Pd2(dba)3 (53 mg, 0.0578 mmol), rac-BINAP (123 mg, 0.198 mmol) and NaOtBu (176 mg, 1.831 mmol) in DMA (5 mL) was heated at 85° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Chromatography on silica (EtOAc/hexanes) afforded 4-chloro-6-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-2H-phthalazin-1-one (15 mg) as a beige solid, 1H (400 MHz, d6-DMSO) δ: 3.21 (m, 4H), 3.40 (m, 4H), 6.86 (d, 1H), 6.91 (d, 1H), 6.98 (s, 1H), 7.05 (m, 1H), 7.22 (t, 1H), 7.38 (dd, 1H), 7.85 (d, 1H), 12.28 (s, 1H) ppm; m/z (M+1) 408.82.

Workup

  1. temperatureto cool
  2. washwashed with water
  3. washThe organic layer was washed with sat.aq
  4. dry with materialNaHCO3, brine and dried (Na2SO4)

Sources & evidence

ORD record
ord-2bf96e7038b1404a8b932c14c772f9c2
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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