4-(2-chloroethoxy)benzoyl Chloride → 3-(4-(2-Chloroethyloxy)phenylmethyl)-4-fluoro-1-(beta-D-glucopyranosyl)indole

HRID 544873Notes

Reaction equation

HRID 544873 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.[Cl: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>>[Cl:34][CH2:35][CH2:36][O:37][C:38]1[CH:46]=[CH:45][C:41]([CH2:42][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:40][CH:39]=1

Participants

3

Reactant 2

HCID 110748714-(2-chloroethoxy)benzoyl ChlorideHCID 670204134-Fluoro-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Product 1

HCID 671954603-(4-(2-Chloroethyloxy)phenylmethyl)-4-fluoro-1-(beta-D-glucopyranosyl)indole

Procedure

4-Fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 2-(3) and 4-(2-chloroethyloxy)benzoyl chloride were treated in a manner similar to Example 3 to give the titled compound as a colorless powder. APCI-Mass m/Z 483/485 (M+NH4). 1H-NMR (DMSO-d6) δ 3.20-3.50 (m, 4H), 3.63-3.70 (m, 2H), 3.91 (t, J=5.1 Hz, 2H), 4.02 (s, 2H), 4.20 (t, J=5.0 Hz, 2H), 4.53 (t, J=5.5 Hz, 1H), 5.09 (d, J=5.3 Hz, 1H), 5.16 (d, J=5.0 Hz, 1H), 5.20 (d, J=5.8 Hz, 1H), 5.37 (d, J=9.2 Hz, 1H), 6.74 (dd, J=11.2, 7.9 Hz, 1H), 6.86 (d, J=8.7 Hz, 2H), 7.07 (m, 1H), 7.18 (d, J=8.5 Hz, 2H), 7.21 (s, 1H), 7.36 (d, J=8.3 Hz, 1H).

Sources & evidence

ORD record
ord-d9194e8b7cfc4b6eaa6cbf1eb9d9f456
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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