4-Fluoropropiophenone → Methyl {4-(2-chlorophenyl)-2-[4-(4-propionylphenoxy)phenyl]thien-3-yl}acetate

HRID 2373707Notes

Reaction equation

HRID 2373707 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[S:11][CH:12]=1.F[C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:35])[CH2:33][CH3:34])=[CH:28][CH:27]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:35])[CH2:33][CH3:34])=[CH:28][CH:27]=3)=[CH:15][CH:14]=2)[S:11][CH:12]=1

Participants

3

Reactant 2

HCID 680044-FluoropropiophenoneHCID 86607176Methyl [4-(2-chlorophenyl)-2-(4-hydroxyphenyl)thien-3-yl]acetate

Product 1

HCID 86607180Methyl {4-(2-chlorophenyl)-2-[4-(4-propionylphenoxy)phenyl]thien-3-yl}acetate

Procedure

Methyl [4-(2-chlorophenyl)-2-(4-hydroxyphenyl)thien-3-yl]acetate was reacted as in Example 9, Step 2 with p-fluoropropiophenone (0.213 g, 1.40 mmol) to yield methyl {4-(2-chlorophenyl)-2-[4-(4-propionylphenoxy)phenyl]thien-3-yl}acetate (0.398 g). This material was reacted as in Example1, Steps 7 and 8 to yield N″-({4-(2-chlorophenyl)-2-[4-(4-propionylphenoxy)phenyl]thien-3-yl}acetyl)guanidine (0.151 g) as a white solid. mp 123-124° C.; 1H NMR (500 MHz, DMSO-d6) δ: 1.04 (t, 3H, J=7.2 Hz), 2.98 (q, 2H, J=7.2 Hz), 3.23 (s, 2H), 7.08 (d, 2H, J=8.9 Hz), 7.14 (d, 2H, J=8.7 Hz), 7.31 (m, 4H), 7.47 (d, 1H, J=8.1 Hz), 7.59 (d, 2H, J=8.7 Hz), 7.96 (d, 2H, J=8.9 Hz). MS (ES) m/z 518.10 ([M+H]+).

Sources & evidence

ORD record
ord-fe701abddbf848ffa6311a95d663067c
Source dataset
uspto-grants-2008_12
Patent number
US07459567B2

Reaction notes

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