Ammonium Chloride → HCID 59821002, compound

HRID 1363657Notes

Reaction equation

HRID 1363657 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1.Br[C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=1.CC(C)([O-])C.[K+].[Cl-].[NH4+]>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].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:16])([F:17])[F:18])=[CH:10][CH:9]=2)=[CH:21][CH:22]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 775951-Bromo-4-tert-butylbenzeneHCID 27607244'-Trifluoromethoxy-biphenyl-2-ylamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 59821002HCID 59821002, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-amino-4′-(trifluoromethoxy)biphenyl (633 mg, 2.50 mmol), 1-bromo-4-(tert-butyl)benzene (533 mg, 2.50 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (124 mg, 0.2 mmol), bis(dibenzylideneacetone)palladium (0) (72 mg, 0.125 mmol), potassium tert-butoxide (1.68 g, 15.0 mmol) and toluene (10 ml) was stirred at 60° for 5 hours under argon atmosphere. After the reaction mixture was cooled to room temperature, saturated aqueous ammonium chloride. The mixture was filtered through celite and extracted with ethyl acetate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1) to give the title compound (857 mg, 89%) as a brown oil.

Workup

  1. filtrationThe mixture was filtered through celite
  2. extractionextracted with ethyl acetate
  3. customThe residue obtained by evaporation of the solvent under reduced pressure
  4. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-56d7453118d24ee69d01e751e7729802
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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