1-Benzofuran-5-carbonyl chloride → 3-(Benzo[b]furan-5-yl-methyl)-4-methyl-1-(beta-D-glucopyranosyl)indole

HRID 544902Notes

Reaction equation

HRID 544902 reaction equation
[CH3:1][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.[O:34]1[CH:38]=[CH:37][C:36]2[CH:39]=[C:40]([C:43](Cl)=O)[CH:41]=[CH:42][C:35]1=2>>[O:34]1[CH:38]=[CH:37][C:36]2[CH:39]=[C:40]([CH2:43][C:4]3[C:3]4[C:7](=[CH:8][CH:9]=[CH:10][C:2]=4[CH3:1])[N:6]([C@@H:11]4[O:28][C@H:27]([CH2:29][OH:30])[C@@H:22]([OH:23])[C@H:17]([OH:18])[C@H:12]4[OH:13])[CH:5]=3)[CH:41]=[CH:42][C:35]1=2

Participants

3

Reactant 2

HCID 27762681-Benzofuran-5-carbonyl chlorideHCID 671958784-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Product 1

HCID 671976303-(Benzo[b]furan-5-yl-methyl)-4-methyl-1-(beta-D-glucopyranosyl)indole

Procedure

The titled compound was prepared from 4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 23-(1) and benzo[b]furan-5-carbonyl chloride in a manner similar to Example 3 as a colorless powder. APCI-Mass m/Z 424 (M−H). 1H-NMR (DMSO-d6) δ 2.40 (s, 3H), 3.23 (td, J=8.9, 5.5 Hz, 1H), 3.39 (td, J=8.8, 5.1 Hz, 1H), 3.42-3.47 (m, 2H), 3.65-3.70 (m, 2H), 4.30 (s, 2H), 4.52 (t, J=5.5 Hz, 1H), 5.07 (d, J=5.3 Hz, 1H), 5.13 (d, J=5.0 Hz, 1H), 5.17 (d, J=5.8 Hz, 1H), 5.35 (d, J=9.0 Hz, 1H), 6.70 (d, J=7.1 Hz, 1H), 6.87 (d, J=1.4 Hz, 1H), 6.98 (m, 1H), 7.14 (s, 1H), 7.17 (dd, J=8.6, 1.4 Hz, 1H), 7.35 (d, J=8.3 Hz, 1H), 7.38 (s, 1H), 7.50 (d, J=8.3 Hz, 1H), 7.93 (d, J=2.1 Hz, 1H).

Sources & evidence

ORD record
ord-c8af7519cb9249abb3fee29e9dd53acc
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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