1-Methylpiperazine → 5-(4-Methylpiperazin-1-yl)-1H-indole

Temperature

130 °C

5-Bromo-1-triisopropylsilyl-indole (5.8 g, 16.4 mmol), N-methylpiperazine (1.8 g, 18 mmol), NaOt-Bu (2.2 g, 23 mmol), Pd(OAc)2 (37 mg, 0.16 mmol), Pt—Bu3 (66 mg, 0.33 mmol) and, xylene (30 mL) were mixed and heated to 130° C. under stirring for 5 h. The crude material was chromatographed on a silica columns 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 (3H, s), 2.64 (4H, t, J=5), 3.19 (4H, t, J=5), 6.44-6.48 (1H, m), 6.95-7.00 (1H, m), 7.16 (1H, d, J=3), 7.18 (1H, d, J=2), 7.29 (1H, d, J=9) and 8.12 (1H, bs).

1. customThe crude material was chromatographed on a silica columns
2. waitConcentration of the main fractions left 5.6 g of an oil which
3. dissolutionwas dissolved in MeCN (10 mL)
4. addition20 mL of a 1 M solution of tetrabutylammonium fluoride in THF was added
5. waitthe mixture left over-night
6. washeluted, with DCM/MeOH 95/5

ORD record

ord-9ba60ed0e78c4e5e9ce275dadb38fe65

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07524839B2