Potassium Carbonate → 5'-(1,3-Benzoxazol-2-yl)-2'-methyl-1,1'-biphenyl-3-carbonitrile

HRID 7689

Reaction equation

HRID 7689 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[C:13]1[CH:14]=[C:15]([C:20]2[O:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[CH:16]=[CH:17][C:18]=1[CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:21]1[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=[C:20]1[C:15]1[CH:16]=[CH:17][C:18]([CH3:19])=[C:13]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[CH:8]=2)[CH:14]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343253-Cyanophenylboronic acidHCID 219909962-(3-Bromo-4-methylphenyl)-1,3-benzoxazole

Product 1

HCID 219909755'-(1,3-Benzoxazol-2-yl)-2'-methyl-1,1'-biphenyl-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-cyano-phenylboronic acid (183 mg, 1.3 mmol), 2-(3-bromo-4-methylphenyl)-1,3-benzoxazole (300 mg, 1.04 mmol), dichlorobis(triphenylphosphine)palladium(II) (36.5 mg, 0.052 mmol), triphenylphosphine (27 mg, 0.104 mmol), and potassium carbonate (287 mg, 2.08 mmol) in degassed DME/H2O (5:1, 18 mL) was heated to 80° C. for 18 h. The mixture was cooled to rt and the two layers were separated and the aqueous layer was extracted with EtOAc (3×). The organics were combined, dried over Na2SO4, and evaporated to dryness to give a clear solid. Purification of the crude by flash chromatography on silica gel eluting with a gradient of EtOAc:hexanes (0 to 30 min: 0 to 20% EtOAc) afforded 5′-(1,3-benzoxazol-2-yl)-2′-methyl-1,1′-biphenyl-3-carbonitrile a colorless solid.

Workup

  1. temperatureThe mixture was cooled to rt
  2. customthe two layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (3×)
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customto give a clear solid
  7. customPurification of the crude by flash chromatography on silica gel eluting with a gradient of EtOAc

Sources & evidence

ORD record
ord-ddda68329a1d47baa4ac6fb0eabd16f4
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

Loading…