Water → N-(4-fluorophenyl)-1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-amine

HRID 454869Notes

Reaction equation

HRID 454869 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.CC1(C)CC(C)OB([C:28](=[CH2:33])[C:29]([F:32])([F:31])[F:30])O1.O.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[C:2]([C:28](=[CH2:33])[C:29]([F:32])([F:31])[F:30])=[N:3][N:4]=[CH:5]3)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 2735133Sodium Carbonate MonohydrateHCID 164142704,4,6-Trimethyl-2-(3,3,3-trifluoroprop-1-en-2-yl)-1,3,2-dioxaborinane2×HCID 86662092HCID 86662092, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-chloro-N-(4-fluorophenyl)phthalazin-6-amine (0.300 g, 1.1 mmol), 4,4,6-trimethyl-2-(1,1,1-trifluoroprop-2-en-2-yl)-1,3,2-dioxaborinane (0.28 mL, 1.5 mmol), tetrakis(triphenylphosphine)palladium (0.063 g, 0.055 mmol) and sodium carbonate monohydrate (0.41 g, 3.3 mmol) in 6 mL of dioxane/water (3/1) was heated in a microwave at 100° C. for 40 min. Additional 4,4,6-trimethyl-2-(1,1,1-trifluoroprop-2-en-2-yl)-1,3,2-dioxaborinane (0.100 mL) and tetrakis(triphenylphosphine)palladium (0.063 g, 0.055 mmol) was added and the mixture was heated at 100° C. for an additional 30 min. After cooling to RT, water was added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified on an ISCO column (12 g, 50-80% EtOAc in hexanes) to afford N-(4-fluorophenyl)-1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-amine as a light yellow solid.

Workup

  1. temperaturethe mixture was heated at 100° C. for an additional 30 min
  2. temperatureAfter cooling to RT
  3. extractionthe mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified on an ISCO column (12 g, 50-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c111a456245549669b36b8a0200d387d
Source dataset
uspto-grants-2013_07
Patent number
US08497269B2

Reaction notes

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