Methanol → [2-(2-Methyl-4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

HRID 609819Notes

Reaction equation

HRID 609819 reaction equation
CN(C)[C:3]1[S:4][C:5]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:6]=2[C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:12][CH:11]=1)=[O:9].[CH3:32][C:33]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:34]=1[Mg]Br.CO>C1COCC1.C(Cl)Cl>[CH3:32][C:33]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:34]=1[C:3]1[S:4][C:5]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:6]=2[C:7]=1[C:8]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:14][CH:15]=1)=[O:9]

Participants

6

Reactant 3

HCID 887MethanolHCID 9954835[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneHCID 178491917HCID 178491917, compound

Product 1

HCID 10720639[2-(2-Methyl-4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneYield 55%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

By the method described in Example 1, [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone (1.6 g, 3.6 mmol) in THF (12 mL) was treated with a 0.65 M THF solution of 2-methyl-4-methoxyphenylmagnesium bromide (20 mL, 13.0 mmol) (prepared from 4-bromo-3-methylanisole, catalytic iodine, and magnesium turnings in THF) to provide, after chromatography (silica gel, 5-10% MeOH in CH2Cl2) 1.02 g (55%) of the title compound as a dark oil: 1H NMR d 1.46 (m, 2H), 1.63 (m, 4H), 2.26 (s, 3H), 2.54 (m, 4H), 2.79 (t, J=5.8 Hz, 2H), 3.47 (s, 3H), 3.89 (s, 3H), 4.12 (t, J=5.8 Hz, 2H), 6.60 (m, 2H), 6.74 (d, J=8.8 Hz, 2H), 6.98 (dd, J=2.4, 8.9 Hz, 1H), 7.19 (d, J=9.3 Hz, 1H), 7.32 (d, J=2.4 Hz, 1H), 7.60 (d, J=8.9 Hz, 1H), 7.69 (d, J=8.8 Hz, 2H); MS (FD) m/e 515 (M+); Anal. calc'd. for C31H33N1O4S1 : C, 72.20; H, 6.45; N, 2.72. Found: C, 72.50; H, 6.56; N, 2.80.

Workup

  1. customto provide

Sources & evidence

ORD record
ord-30e2f13898a946d6ba6ad593c351783f
Source dataset
uspto-grants-1999_12
Patent number
US05998442

Reaction notes

Loading…