Iodobenzene → HCID 86720787, compound

HRID 1776075Notes

Reaction equation

HRID 1776075 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[CH3:17].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:17][C:11]1[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:10]=1[N:9]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 11575IodobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 21989085Bis(2,4-dimethylphenyl)amine2×HCID 23676156Sodium t-butoxide

Product 1

HCID 86720787HCID 86720787, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of bis(2,4-dimethylphenyl)amine (Compound 14) (9.4 g, 41.8 mmol), iodobenzene (17.14 g, 84 mmol), Pd(OAc)2 (0.47 g, 2.1 mmol), P(t-Bu)3 (0.848 g, 4.2 mmol), sodium tert-butoxide (7.68 g, 80 mmol) in toluene (120 mL) was degassed and heated at 120° C. for 16 hours. The resulting mixture was poured into ethyl acetate (250 mL), washed with brine, dried over Na2SO4, loaded on silicagel and purified by flash column using eluent of hexanes. After removal of solvent, an oil (Compound 15) was obtained (12.4 g, in 98.6% yield).

Workup

  1. customwas degassed
  2. additionThe resulting mixture was poured into ethyl acetate (250 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. custompurified by flash column
  6. customAfter removal of solvent

Sources & evidence

ORD record
ord-36b08ece49f54023898e319f0f78bc8d
Source dataset
uspto-grants-2016_02
Patent number
US09263681B2

Reaction notes

Loading…