N-(4-fluorophenyl)-1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-amine → N-(4-Fluorophenyl)-1-(2,2,2-trifluoro-1-methylethyl)-6-phthalazinamine

HRID 454870Notes

Reaction equation

HRID 454870 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19](=[CH2:24])[C:20]([F:23])([F:22])[F:21])=[N:14][N:13]=[CH:12]3)=[CH:4][CH:3]=1.[H][H]>C1COCC1.CCO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([CH:19]([CH3:24])[C:20]([F:22])([F:21])[F:23])=[N:14][N:13]=[CH:12]3)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 66740077N-(4-fluorophenyl)-1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 45280246N-(4-Fluorophenyl)-1-(2,2,2-trifluoro-1-methylethyl)-6-phthalazinamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of N-(4-fluorophenyl)-1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-amine (0.067 g, 0.20 mmol) in 4 mL of THF/EtOH (3/1) was treated with palladium (10% wt. on activated carbon, 0.021 g, 0.020 mmol); and stirred at RT with a balloon of hydrogen. After 3 h, the reaction mixture was filtered through a pad of Celite and the filtrate was concentrated to give the crude product. The material was purified on an ISCO column (12 g, 50-75% EtOAc in hexanes) to afford the title compound as a light yellow solid. MS (ESI, pos. ion) m/z: M+1=366.0.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product
  4. customThe material was purified on an ISCO column (12 g, 50-75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3530fa45ef50491a87db87ffb8178493
Source dataset
uspto-grants-2013_07
Patent number
US08497269B2

Reaction notes

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