5-Ethylthiophene-2-carbonyl chloride → 3-(5-Ethylthiophen-2-yl-methyl)-4-fluoro-1-(beta-D-glucopyranosyl)indole
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][O:30]C(=O)C)[C@@H:22]([O:23]C(=O)C)[C@H:17]([O:18]C(=O)C)[C@H:12]1[O:13]C(=O)C.[CH2:34]([C:36]1[S:40][C:39]([C:41](Cl)=O)=[CH:38][CH:37]=1)[CH3:35]>>[CH2:34]([C:36]1[S:40][C:39]([CH2:41][C:4]2[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[F:1])[N:6]([C@@H:11]3[O:28][C@H:27]([CH2:29][OH:30])[C@@H:22]([OH:23])[C@H:17]([OH:18])[C@H:12]3[OH:13])[CH:5]=2)=[CH:38][CH:37]=1)[CH3:35]Participants
3
Procedure
4-Fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 2-(3) and 5-ethylthiophen-2-carbonyl chloride were treated in a manner similar to Example 2-(4), (5), (6) and (7) to give the titled compound as a colorless powder. APCI-Mass m/Z 439 (M+NH4). 1H-NMR (DMSO-d6) δ 1.17 (t, J=7.5 Hz, 3H), 2.69 (q, J=7.5 Hz, 2H), 3.20-3.48 (m, 4H), 3.67 (m, 2H), 4.20 (s, 2H), 4.53 (br, 1H), 5.08 (br, 1H), 5.20 (br, 2H), 5.38 (d, J=9.2 Hz, 1H), 6.60 (d, J=3.3 Hz, 1H), 6.65 (d, J=3.2 Hz, 1H), 6.77 (dd, J=11.1, 7.8 Hz, 1H), 7.09 (m, 1H), 7.31 (s, 1H), 7.39 (d, J=8.3 Hz, 1H).
Sources & evidence
- ORD record
- ord-790043d5e91545c7956ea0a39309ecff
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935674B2
Reaction notes
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