4-Fluorophenylboronic acid → HCID 67196395, compound

HRID 544910Notes

Reaction equation

HRID 544910 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.[F:41][C:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1>>[F:41][C:42]1[CH:47]=[CH:46][C:45]([C:2]2[S:6][C:5]([CH2:7][C:8]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][C:15]=4[CH3:17])[N:10]([C@@H:18]4[O:35][C@H:34]([CH2:36][OH:37])[C@@H:29]([OH:30])[C@H:24]([OH:25])[C@H:19]4[OH:20])[CH:9]=3)=[CH:4][CH:3]=2)=[CH:44][CH:43]=1

Participants

3

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 67199228HCID 67199228, compound

Product 1

HCID 67196395HCID 67196395, 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 4-fluorobenzeneboronic acid were treated in a manner similar to Example 45-(4) and 2-(7) to give the titled compound as a yellow powder. APCI-Mass m/Z 484 (M+H). 1H-NMR (DMSO-d6) δ 2.50 (s, 3H), 3.25 (td, J=8.8, 5.4 Hz, 1H), 3.40 (td, J=9.0, 5.4 Hz, 1H), 3.43-3.48 (m, 2H), 3.67-3.71 (m, 2H), 4.37 (s, 2H), 4.54 (t, J=5.5 Hz, 1H), 5.09 (d, J=5.1 Hz, 1H), 5.15 (d, J=5.1 Hz, 1H), 5.17 (d, J=6.1 Hz, 1H), 5.36 (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=7.7 Hz, 1H), 7.19 (t, J=8.8 Hz, 2H), 7.30 (d, J=3.5 Hz, 1H), 7.32 (s, 1H), 7.36 (d, J=8.3 Hz, 1H), 7.59 (dd, J=8.7, 5.3 Hz, 2H).

Sources & evidence

ORD record
ord-d08ede25f68e45769fd2b58a14558dc7
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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