Sodium Carbonate → (4-Tert-butyl-phenyl)-[6-(2-trifluoromethyl-phenyl)-phthalazin-1-yl]-amine

HRID 1791210Notes

Reaction equation

HRID 1791210 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)=[N:7][N:6]=[CH:5]2.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:8]2[C:9]3[C:4](=[CH:3][C:2]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[C:24]([F:35])([F:34])[F:23])=[CH:11][CH:10]=3)[CH:5]=[N:6][N:7]=2)=[CH:14][CH:15]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 22030046(6-Bromo-phthalazin-1-yl)-(4-tert-butyl-phenyl)-amine

Product 1

HCID 22030022(4-Tert-butyl-phenyl)-[6-(2-trifluoromethyl-phenyl)-phthalazin-1-yl]-amine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Combine (6-bromo-phthalazin-1-yl)-(4-tert-butyl-phenyl)-amine (60 mg, 0.19 mmol), 2-(trifluoromethyl)phenyl-boronic acid (50 mg, 0.26 mmol) in 1,2-dimethoxyethane (10 mL) and bubble nitrogen into the mixture for 10 minutes. Add tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.01 mmol) and 2M Na2CO3 (1 mL) and heat at 80 C. for 48 hours. Let the mixture cool to room temperature, dilute with water (10 mL), and extract twice with EtOAc (10 mL each). Dry (Na2SO4), evaporate, and purify on a preparative silica gel plate (2000 micron) eluting with 75% hexane-EtOAc to provide (4-tert-butyl-phenyl)-[6-(2-trifluoromethyl-phenyl)-phthalazin-1-yl]-amine as a straw colored solid. Mass Spec. 421.2.

Workup

  1. extractionextract twice with EtOAc (10 mL each)
  2. dry with materialDry (Na2SO4)
  3. customevaporate
  4. custompurify on a preparative silica gel plate (2000 micron)
  5. washeluting with 75% hexane-EtOAc

Sources & evidence

ORD record
ord-f05793046f79432d89909773a45ee04d
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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