4-Methoxycarbonylphenylboronic acid → Methyl 4-(3-{[(3-Methoxy-5-Methylpyrazin-2-yl)[(2-Methylpropoxy)carbonyl]aMino]sulfonyl}pyridin-2-yl)benzoate

HRID 1861028Notes

Reaction equation

HRID 1861028 reaction equation
Cl[C:2]1[C:7]([S:8]([N:11]([C:21]([O:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[O:22])[C:12]2[C:17]([O:18][CH3:19])=[N:16][C:15]([CH3:20])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:28][O:29][C:30]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)=[O:31]>>[CH2:24]([O:23][C:21]([N:11]([C:12]1[C:17]([O:18][CH3:19])=[N:16][C:15]([CH3:20])=[CH:14][N:13]=1)[S:8]([C:7]1[C:2]([C:35]2[CH:36]=[CH:37][C:32]([C:30]([O:29][CH3:28])=[O:31])=[CH:33][CH:34]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)(=[O:10])=[O:9])=[O:22])[CH:25]([CH3:27])[CH3:26]

Participants

3

Reactant 2

HCID 27343694-Methoxycarbonylphenylboronic acidHCID 11015197Isobutyl (2-chloropyridin-3-yl)sulfonyl(3-methoxy-5-methylpyrazin-2-yl)carbamate

Product 1

HCID 22325614Methyl 4-(3-{[(3-Methoxy-5-Methylpyrazin-2-yl)[(2-Methylpropoxy)carbonyl]aMino]sulfonyl}pyridin-2-yl)benzoate

Procedure

reaction of 2-chloro-N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulfonamide with 4-methoxycarbonylphenylboronic acid (or an anhydride or ester thereof) in the presence of a source of fluoride ion and under aqueous conditions to give N-(isobutoxycarbonyl)-2-(4-methoxycarbonylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl) pyridine-3-sulfonamide;

Sources & evidence

ORD record
ord-f8381ba5fee64896af01a430891a135f
Source dataset
uspto-grants-2003_03
Patent number
US06531605B1

Reaction notes

Loading…