(6-Fluoropyridin-3-yl)boronic acid → HCID 67197126, compound

HRID 544911Notes

Reaction equation

HRID 544911 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[N:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1>>[F:41][C:42]1[N: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 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 67199228HCID 67199228, compound

Product 1

HCID 67197126HCID 67197126, 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 6-fluoropyridine-3-boronic acid were treated in a manner similar to Example 45-(4) and 2-(7) to give the titled compound as a colorless powder. APCI-Mass m/Z 485 (M+H). 1H-NMR (DMSO-d6) δ 2.50 (s, 3H), 3.20-3.50 (m, 4H), 3.70 (m, 2H), 4.40 (s, 2H), 4.54 (t, J=5.4 Hz, 1H), 5.09 (d, J=5.3 Hz, 1H), 5.16 (d, J=5.7 Hz, 1H), 5.17 (d, J=5.7 Hz, 1H), 5.36 (d, J=9.0 Hz, 1H), 6.75 (d, J=7.1 Hz, 1H), 6.87 (d, J=3.4 Hz, 1H), 7.00 (t, J=7.7 Hz, 1H), 7.19 (dd, J=8.6, 2.7 Hz, 1H), 7.33 (s, 1H), 7.37 (d, J=8.2 Hz, 1H), 7.44 (d, J=3.4 Hz, 1H), 8.16 (dt, J=8.2, 2.4 Hz, 1H), 8.45 (d, J=2.3 Hz, 1H).

Sources & evidence

ORD record
ord-3d922fafacb44a7f9664e27188f9051d
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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