4-(2-Fluoroethoxy)benzoyl chloride → 4-Fluoro-3-(4-(2-fluoroethyloxy)phenylmethyl)-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.[F:34][CH2:35][CH2:36][O:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=O)=[CH:40][CH:39]=1>>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:42][C:41]1[CH:40]=[CH:39][C:38]([O:37][CH2:36][CH2:35][F:34])=[CH:46][CH:45]=1)=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][OH:30])[C@@H:22]([OH:23])[C@H:17]([OH:18])[C@H:12]1[OH:13]Participants
3
Procedure
4-Fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 2-(3) and 4-(2-fluoroethyloxy)benzoyl 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 467 (M+NH4). 1H-NMR (DMSO-d6) δ 3.15-3.41 (m, 4H), 3.65 (m, 2H), 4.01 (s, 2H), 4.12 (m, 1H), 4.22 (dd, J=4.7, 3.2 Hz, 1H), 4.53 (t, J=5.5 Hz, 1H), 4.63 (m, 1H), 4.78 (m, 1H), 5.09 (d, J=5.3 Hz, 1H), 5.16 (d, J=5.0 Hz, 1H), 5.21 (d, J=5.9 Hz, 1H), 5.36 (d, J=9.1 Hz, 1H), 6.74 (dd, J=11.4, 7.8 Hz, 1H), 6.87 (d, J=8.6 Hz, 2H), 7.06 (dt, J=8.1, 5.2 Hz, 1H), 7.18 (d, J=8.6 Hz, 2H), 7.20 (s, 1H), 7.35 (d, J=8.4 Hz, 1H).
Sources & evidence
- ORD record
- ord-9fa43d0559b84051ad818f79273ec5d9
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935674B2
Reaction notes
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