Carbon tetrabromide → Methyl 1-({4-ethyl-5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methyl)azetidine-3-carboxylate
Reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:26]O)[S:6][C:7]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)[O:10][N:9]=1)[CH3:2].C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:53]1[CH2:56][CH:55]([C:57]([O:59][CH3:60])=[O:58])[CH2:54]1.C(N(CC)C(C)C)(C)C>>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:26][N:53]2[CH2:56][CH:55]([C:57]([O:59][CH3:60])=[O:58])[CH2:54]2)[S:6][C:7]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)[O:10][N:9]=1)[CH3:2]Participants
Reactant 5
Product 1
Procedure
The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 1 (1f) using {4-ethyl-5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methanol (0.17 g, 0.44 mmol) that was obtained in Example 13 (13a), carbon tetrabromide (0.19 g, 0.57 mmol), triphenylphosphine (0.15 g, 0.57 mmol), methyl 3-azetidinecarboxylate hydrochloride (0.10 g, 0.66 mmol), and N,N-diisopropylethylamine (0.23 mL, 1.3 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:3 to 1:2) as the eluent to afford the title compound (0.19 g) in a yield of 89% as a pale yellow oily product.
Workup
- customthe reaction similar to
Sources & evidence
- ORD record
- ord-1d725090f34b4ab9a5c60ace6c54ed3b
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
Loading…