Réaction #8433

Équation de réaction

5-Bromo-1-triisopropylsilyl-indole

N-methylpiperazine

NaOt-Bu

→

product

Rendement 57.0%

5-(4-Methylpiperazin-1-yl)-indole

Rendement 57.0%

Solvants

xylene

Conditions de réaction

Traitement

1. 1
   AutreThe crude material was chromatographed on a silica column
2. 2
   workup.WAITConcentration of the main fractions left 5.6 g of an oil which
3. 3
   workup.DISSOLUTIONwas dissolved in MeCN (10 mL)
4. 4
   workup.ADDITION20 mL of a 1 M solution of tetrabutylammonium fluoride in THF was added
5. 5
   workup.WAITthe mixture left over-night
6. 6
   Lavageeluted with DCM/MeOH 95/5

Mode opératoire

5-Bromo-1-triisopropylsilyl-indole (5.8 g, 16.4 mmol), N-methylpiperazine (1.8 g, 18 numol), NaOt-Bu (2.2 g, 23 mmol), Pd(OAc)2 (37 mg, 0.16 mmol), Pt-Bu3 (66 mg, 0.33 nmmol) and xylene (30 mL) were mixed and heated to 130° C. under stirring for 5 h. The crude material was chromatographed on a silica column using DCM/MeOH 95/5 as eluent. Concentration of the main fractions left 5.6 g of an oil which was dissolved in MeCN (10 mL), 20 mL of a 1 M solution of tetrabutylammonium fluoride in THF was added and the mixture left over-night. The reaction mixture was put on a silica column and eluted with DCM/MeOH 95/5 to give the product as an oil (2 g, 9.3 mmol; yield 57 %) 1H NMR (CDCl3) δ 2.37 (3 H, s), 2.64 (4 H, t, J=5), 3.19 (4 H, t, J=5), 6.44–6.48 (1 H, m), 6.95–7.00 (1 H, m), 7.16 (1 H, d, J=3), 7.18 (1 H, d, J=2), 7.29 (1H, d, J=9) and 8.12 (1 H, bs).

Source