1-Bromo-4-fluorobenzene → HCID 89586304, compound

HRID 1747807Notes

Reaction equation

HRID 1747807 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[C:17](=[O:18])[CH:16]=[CH:15][N:14]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[N:13]=3)=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[F:32][C:29]1[CH:30]=[CH:31][C:26]([N:22]2[CH2:23][CH2:24][CH:19]([N:14]3[CH:15]=[CH:16][C:17](=[O:18])[C:12]([C:11]4[N:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[N:8]=[CH:9][CH:10]=4)=[N:13]3)[CH2:20][CH2:21]2)=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 99931-Bromo-4-fluorobenzeneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 68014851HCID 68014851, compound

Product 1

HCID 89586304HCID 89586304, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 3-(1-phenyl-1H-pyrazol-5-yl)-1-piperidin-4-ylpyridazin-4(1H)-one (0.30 g), 1-bromo-4-fluorobenzene (0.21 mL), Pd2(dba)3 (43 mg), X-phos (45 mg) and sodium tert-butoxide (135 mg) in toluene (10 mL) was stirred at 120° C. for 5 hr under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane to give the title compound (0.32 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  6. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d2b8ab7c92a249548ad358ee1d181d41
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

Loading…