4-Iodobenzoyl chloride → 3-(4-Iodophenylmethyl)-4-methyl-1-(beta-D-glucopyranosyl)indole

HRID 544901Notes

Reaction equation

HRID 544901 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.[I:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=O)=[CH:37][CH:36]=1>>[I:34][C:35]1[CH:43]=[CH:42][C:38]([CH2:39][C:4]2[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[CH3:1])[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:37][CH:36]=1

Participants

3

Reactant 2

HCID 743734-Iodobenzoyl chlorideHCID 671958784-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Product 1

HCID 671992783-(4-Iodophenylmethyl)-4-methyl-1-(beta-D-glucopyranosyl)indole

Procedure

4-Methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 23-(1) and 4-iodobenzoyl chloride were treated in a manner similar to Example 27 to give the titled compound as a colorless powder. APCI-Mass m/Z 510 (M+H). 1H-NMR (DMSO-d6) δ 2.38 (s, 3H), 3.24 (m, 1H), 3.30-3.47 (m, 4H), 3.68 (m, 1H), 4.16 (s, 2H), 4.52 (t, J=5.6 Hz, 1H), 5.08 (d, J=5.3 Hz, 1H), 5.14 (d, J=5.0 Hz, 1H), 5.16 (d, J=5.9 Hz, 1H), 5.34 (d, J=9.0 Hz, 1H), 6.71 (d, J=7.1 Hz, 1H), 6.98 (dd, J=8.3, 6.9 Hz, 1H), 6.99 (d, J=8.2 Hz, 2H), 7.15 (s, 1H), 7.35 (d, J=8.3 Hz, 1H), 7.46 (d, J=8.2 Hz, 2H).

Sources & evidence

ORD record
ord-996b29d702744abd82fe6cc700d6dee1
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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