Phenylboronic Acid → HCID 21186295, compound

HRID 1384195Notes

Reaction equation

HRID 1384195 reaction equation
CO.[N+](C1C=C(C=CC=1)CO)([O-])=O.C(OC([N:21]([C:37]1[C:42]([O:43][CH3:44])=[N:41][C:40]([CH3:45])=[CH:39][N:38]=1)[S:22]([C:25]1[C:26]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:27][CH:28]=[CH:29][CH:30]=1)(=[O:24])=[O:23])=O)C(C)C.C1(B(O)O)C=CC=CC=1>>[CH3:44][O:43][C:42]1[C:37]([NH:21][S:22]([C:25]2[C:26]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:27][CH:28]=[CH:29][CH:30]=2)(=[O:24])=[O:23])=[N:38][CH:39]=[C:40]([CH3:45])[N:41]=1

Participants

4

Reactant 3

HCID 66827Phenylboronic AcidHCID 21186305HCID 21186305, compoundHCID 70066851HCID 70066851, compound

Product 1

HCID 21186295HCID 21186295, compound

Procedure

1H NMR (d6-DMSO): 2.2 (s, 3H), 3.6 (s, 3H), 7.3-7.55 (m, 6H), 7.6 (dd, 1H), 8.4 (dd, 1H), 8.8 (dd, 1H), 10.5 (br s, 1H); mass spectrum (positive fast atom bombardment (+ve FAB), methanol/m-nitrobenzyl alcohol (NBA)): 357 (M+H)+; starting from N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-2-phenylpyridine-3-sulphonamide; 1H NMR (d6-DMSO): 0.6 (d, 6H), 1.7 (m, 1H), 2.55 (s, 3H), 3.7 (d, 2H), 3.9 (s, 3H), 7.4-7.55 (m, 5H), 7.8 (dd, 1H), 8.9 (dd, 1H), 8.95 (dd, 1H); mass spectrum (+ve CI): 457 (M+H)+; itself obtained using an analogous procedure to that described in Example 1, part (iii) but using phenylboronic acid.

Workup

  1. customitself obtained

Sources & evidence

ORD record
ord-8fcd34e07bd449018ecab535b6c936a0
Source dataset
uspto-grants-2001_07
Patent number
US06258817B1

Reaction notes

Loading…