Water → 3-(1-(2,4-bis(trifluoromethyl)phenyl)phthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide

HRID 2357539Notes

Reaction equation

HRID 2357539 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:15]([NH:17][CH:18]3[CH2:20][CH2:19]3)=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.[F:25][C:26]([F:41])([F:40])[C:27]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:28]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.CCO.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:25][C:26]([F:40])([F:41])[C:27]1[CH:32]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:30]=[CH:29][C:28]=1[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=3[CH3:24])[C:15]([NH:17][CH:18]3[CH2:20][CH2:19]3)=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27826672,4-Bis(trifluoromethyl)phenylboronic acidHCID 118483123-(1-chlorophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide

Product 1

HCID 118489893-(1-(2,4-bis(trifluoromethyl)phenyl)phthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 20074477Dimethoxyethane ethanolSolvent

Conditions

Temperature
120 °C

Procedure

In a microwave tube was placed 3-(1-chlorophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide (0.097 g, 0.29 mmol), 2,4-bis(trifluoromethyl)benzeneboronic acid (0.074 g, 0.29 mmol), tetrakis(triphenylphosphine)palladium (0) (0.033 g, 0.029 mmol) and 2M potassium carbonate (0.43 mL, 0.86 mmol) in 1.5 mL of DME/EtOH (4/1). The mixture was heated in the microwave at 120° C. for 20 minutes. After cooling, water was added and the mixture was extracted with DCM. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude product was purified by HPLC to give 3-(1-(2,4-bis(trifluoromethyl)phenyl)phthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide as an off-white solid. MS (ES+)=516.2 (M+H).

Workup

  1. customIn a microwave tube was placed
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with DCM
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-813e4658880a4a7a9517b53ed6c36131
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

Loading…