N-Methylaniline → HCID 10752511, compound

HRID 412770Notes

Reaction equation

HRID 412770 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.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.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:13]([CH3:12])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 7515N-MethylanilineHCID 775951-Bromo-4-tert-butylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 10752511HCID 10752511, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

According to general procedure B, 4-tert-butylbromobenzene (117 mg, 0.55 mmol) reacted with N-methylaniline (54 mg, 0.50 mmol) using 1 mol % of Pd(dba)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (58 mg, 0.60 mmol) in toluene at 100° C. for 2 h to give the title compound (117 mg, 98%): 1H-NMR (300 MHz, CDCl3): δ 7.36 (t, 2H, J=8.1 Hz), 7.29 (t, 2H, J=7.5 and 7.8 Hz), 7.04 (dd, 4H, J=8.1 Hz), 6.94 (t, 1H, J=7.2 Hz and 7.5 Hz), 3.34 (s, 3H), 1.38 (s, 9H). 13C{1H}-NMR (100 MHz, CDCl3): δ 149.17, 146.36, 144.77, 129.02, 126.05, 121.23, 120.18, 118.94, 40.20, 34.18, 31.45. GC/MS(EI): m/z 239 (M+), 224

Workup

  1. customat 100° C.
  2. customfor 2 h

Sources & evidence

ORD record
ord-3cc2eb29e3fa49e395d66e1f3cdba14f
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

Loading…