Phenylboronic Acid → HCID 67196719, compound

HRID 544912Notes

Reaction equation

Br[C:2]1[S:6][C:5]([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH3:17])[N:10]([C@@H:18]3[O:35][C@H:34]([CH2:36][O:37]C(=O)C)[C@@H:29]([O:30]C(=O)C)[C@H:24]([O:25]C(=O)C)[C@H:19]3[O:20]C(=O)C)[CH:9]=2)=[CH:4][CH:3]=1.[C:41]1(B(O)O)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[CH3:17][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[C:8]([CH2:7][C:5]1[S:6][C:2]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:3][CH:4]=1)=[CH:9][N:10]2[C@@H:18]1[O:35][C@H:34]([CH2:36][OH:37])[C@@H:29]([OH:30])[C@H:24]([OH:25])[C@H:19]1[OH:20]

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 67199228HCID 67199228, compound

Product 1

HCID 67196719HCID 67196719, compound

Procedure

3-(5-Bromothiophen-2-yl-methyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 45-(3) and benzeneboronic acid were treated in a manner similar to Example 45-(4) and 2-(7) to give the titled compound as a pale yellow powder. APCI-Mass m/Z 466 (M+H). 1H-NMR (DMSO-d6) δ 2.50 (s, 3H), 3.25 (m, 1H), 3.35-3.49 (m, 2H), 3.66-3.73 (m, 2H), 4.38 (s, 2H), 4.54 (t, J=5.5 Hz, 1H), 5.09 (d, J=5.3 Hz, 1H), 5.15 (d, J=5.0 Hz, 1H), 5.17 (d, J=5.9 Hz, 1H), 5.37 (d, J=9.2 Hz, 1H), 6.75 (d, J=7.1 Hz, 1H), 6.80 (d, J=3.5 Hz, 1H), 7.00 (t, J=7.6 Hz, 1H), 7.24 (t, J=7.3 Hz, 1H), 7.31-7.38 (m, 5H), 7.56 (d, J=7.4 Hz, 2H).

Sources & evidence

ORD record: ord-aeb65a89fb994010aa2136eff36698e8
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935674B2

Reaction notes

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