Indole → N-(4-methylphenyl)indole

Participants

Role	Name	HCID	Charge
Reactant	Indole	HCID 798	—
Reactant	4-Chlorotoluene	HCID 7810	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Tris(1,1-dimethylethyl)phosphine	HCID 83681	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	Toluene	HCID 1140	—
Product	N-(4-methylphenyl)indole	HCID 9794286	66.1%

Reaction Steps

Soc., Jpn., 55:1116-1120 (1982)). The above general procedure was followed using of 4-chlorotoluene (126 mg, 1.00 mmol), indole (117 mg, 1.00 mmol), 4 mol % Pd(dba)2, 4 mol % tri-t-butylphosphine, and cesium carbonate (1.50) in 1.0 mL of toluene. After 12 hours at 100° C., the reaction mixture was adsorbed onto silica gel and chromatographed with 10% ethyl acetate/hexanes to give 137 mg (66%) of N-(4-methylphenyl)indole. 1H NMR (500 MHz, CDCl3) δ 7.70 (d, J=7.8 Hz, 1H), 7.54 (d, J=8.2 Hz, 1H), 7.40 (d, J=7.8 Hz, 2H), 7.34-7.33 (m, 3H), 7.23 (t, J=7.8 Hz, 1H), 7.18 (t, J=7.8 Hz, 1H), 5 6.68 (d, J=2.4 Hz, 1H), 2.46 (s, 3H). 13C NMR (125 MHz, CDCl3) δ 137.4, 136.4, 136.1, 130.2, 129.3, 128.2, 124.4, 122.3, 121.2, 120.3, 110.6, 103.3, 21.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06100398
Source dataset	uspto-grants-2000_08
ORD ID	ord-795fadbc0f284c529f1b1d0f349d7267
Source note	uspto-grants-2000_08