Methanol → HCID 15429201, compound

HRID 609816Notes

Reaction equation

HRID 609816 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].C1COCC1.[CH3:37][O:38][C:39]1[CH:40]=[C:41]([Mg]Br)[CH:42]=[CH:43][CH:44]=1.CO>ClC1C=CC=CC=1.C(Cl)Cl>[CH3:37][O:38][C:39]1[CH:44]=[C:43]([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[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)=[CH:12][CH:11]=2)=[O:9])[CH:42]=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 9954835[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneHCID 178490745HCID 178490745, compound

Product 1

HCID 15429201HCID 15429201, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7964ChlorobenzeneSolvent

Procedure

By the method described in Example 1, [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone (1.0 g, 2.29 mmol) in chlorobenzene (10 mL) was treated with a 0.64 M THF solution of 3-methoxyphenylmagnesium bromide (11.0 mL, 7.04 mmol) (prepared from 3-bromoanisole, catalytic iodide, and magnesium turnings in THF) to provide after chromatography (silica gel, 5-10% MeOH in CH2Cl2) 610 mg (53%) of the title compound as a dark oil: 1H NMR d 1.44 (m, 2H), 1.59 (m, 4H), 2.47 (m, 4H), 2.73 (t, J=6.0 Hz, 2H), 3.70 (s, 3H), 3.88 (s, 3H), 4.08 (t, J=6.0 Hz, 2H), 6.76 (m, 3H), 6.96-7.04 (m, 3H), 7.15 (t, J=8.0 Hz, 1H), 7.33 (d, J=2.0 Hz, 1H), 7.56 (d, J=8.9 Hz, 1H), 7.78 (d, J=8.7 Hz, 2H); MS (FD) m/e 501 (M+); Anal. calc'd. for C30H31NO4S: C, 71.83; H, 6.23; N, 2.79. Found: C, 71.68; H, 6.25; N, 2.66.

Sources & evidence

ORD record
ord-f05d6acc93c7453e8af571e017df216e
Source dataset
uspto-grants-1999_12
Patent number
US05998442

Reaction notes

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