Phenethylamine, m-trifluoromethyl- → HCID 86593831, compound

HRID 912905Notes

Reaction equation

HRID 912905 reaction equation
Br[C:2]1[C:34]([C:35]([F:38])([F:37])[F:36])=[CH:33][C:5]2[N:6]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:7]([N:9]3[CH2:14][CH2:13][N:12]([C:15]4[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=4)[CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1.[F:39][C:40]([F:51])([F:50])[C:41]1[CH:42]=[C:43]([CH2:47][CH2:48][NH2:49])[CH:44]=[CH:45][CH:46]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.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]>[F:39][C:40]([F:50])([F:51])[C:41]1[CH:42]=[C:43]([CH2:47][CH2:48][NH:49][C:2]2[C:34]([C:35]([F:38])([F:37])[F:36])=[CH:33][C:5]3[N:6]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:7]([N:9]4[CH2:14][CH2:13][N:12]([C:15]5[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=5)[CH2:11][CH2:10]4)=[N:8][C:4]=3[CH:3]=2)[CH:44]=[CH:45][CH:46]=1

Participants

8

Reactant 4

HCID 104223Phenethylamine, m-trifluoromethyl-HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 11606965HCID 11606965, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 86593831HCID 86593831, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of the product from step (a) above (88 mg, 0.14 mmol), 2-(3-trifluoromethylphenyl)ethylamine (45 mg, 0.24 mmol, Trans World Chemicals), tris(dibenzylideneacetone)dipalladium(0) (8 mg, 0.01 mmol, Strem), 2-(di-t-butylphosphino)biphenyl (8 mg, 0.03 mmol, Strem) and sodium-tert-butoxide (31 mg, 0.33 mmol, Aldrich) in toluene (2 mL) was heated at 150° C. in a microwave synthesizer for 14 min. The reaction mixture was cooled to room temperature, diluted with EtOAc (5 mL) and filtered through a Celite® pad. The filtrate was concentrated in vacuo and the residue dissolved in MeOH (4 mL), and purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile) to give the title compound as pale-yellow oil. MS (ESI, pos. ion) m/z: 733 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through a Celite® pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue dissolved in MeOH (4 mL)
  5. custompurified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile)

Sources & evidence

ORD record
ord-e6d4c284d3dc4673bfcc481424de9efd
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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