Iodine → [2-(3-(t-Butyldimethylsilyl)oxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

HRID 609818Notes

Reaction equation

HRID 609818 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].[Si:32]([O:39][C:40]1[CH:41]=[C:42]([Mg]Br)[CH:43]=[CH:44][CH:45]=1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].II.[Mg]>C1COCC1.C(Cl)Cl.CO>[Si:32]([O:39][C:40]1[CH:41]=[C:42]([C:3]2[S:4][C:5]3[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:6]=3[C:7]=2[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:12][CH:11]=2)=[O:9])[CH:43]=[CH:44][CH:45]=1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]

Participants

8

Reactant 4

HCID 807IodineHCID 5462224MagnesiumHCID 9954835[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneHCID 178455064HCID 178455064, compound

Product 1

HCID 10793714[2-(3-(t-Butyldimethylsilyl)oxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneYield 73.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

By the method described in Example 1, [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone (1.6 g, 3.75 mmol) in THF (15 mL) was treated with a 0.6 M THF solution of 3-(t-butyldimethylsilyloxy)phenylmagnesium bromide (16 mL, 9.60 mmol) (prepared from the product of preparation 3, catalytic iodine, and magnesium turnings in THF) to provide, after chromatography (silica gel, 5-10% MeOH in CH2Cl2) 1.65 g (73%) of the title compound as a yellow oil: 1H NMR d 0.11 (s, 6H), 0.95 (s, 9H), 1.45 (m, 2H), 1.61 (m, 4H), 2.50 (m, 4H), 2.76 (t, J=5.9 Hz, 2H), 3.89 (s, 3H), 4.09 (t, J=5.9 Hz, 2H), 6.69 (d, J=8.5 Hz, 1H), 6.77 (d, J=8.5 Hz, 2H), 6.90 (s, 1H), 6.96-7.10 (m, 3H), 7.34 (m, 1H), 7.55 (d, J=8.8 Hz, 1H), 7.78 (d, J=8.2 Hz, 2H); MS (FD) m/e 601 (M+); Anal. calc'd. for C35H43NO4SSi: C, 69.85; H, 7.20; N, 2.33. Found: C, 69.83; H, 7.34; N, 2.34.

Workup

  1. customto provide

Sources & evidence

ORD record
ord-25abcc52be174989ad0de6683c714d25
Source dataset
uspto-grants-1999_12
Patent number
US05998442

Reaction notes

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