2-Methoxy-6-methylpyridine-3-boronic acid → N-(4-{(E)-2-[3-tert-butyl-2-methoxy-5-(2-methoxy-6-methyl-pyridin-3-yl)-phenyl]-vinyl}-3-methoxymethyl-phenyl)-methanesulfonamide

HRID 2390854Notes

Reaction equation

HRID 2390854 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:5]([O:24][CH3:25])=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][C:11]=2[CH2:21][O:22][CH3:23])[CH:7]=1.[CH3:30][C:31]1[N:36]=[C:35]([O:37][CH3:38])[C:34](B(O)O)=[CH:33][CH:32]=1>>[C:26]([C:4]1[C:5]([O:24][CH3:25])=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][C:11]=2[CH2:21][O:22][CH3:23])[CH:7]=[C:2]([C:34]2[C:35]([O:37][CH3:38])=[N:36][C:31]([CH3:30])=[CH:32][CH:33]=2)[CH:3]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

3

Reactant 2

HCID 27631212-Methoxy-6-methylpyridine-3-boronic acidHCID 67286866N-{4-[(E)-2-(5-bromo-3-tert-butyl-2-methoxy-phenyl)-vinyl]-3-methoxymethyl-phenyl}-methanesulfonamide

Product 1

HCID 67070031N-(4-{(E)-2-[3-tert-butyl-2-methoxy-5-(2-methoxy-6-methyl-pyridin-3-yl)-phenyl]-vinyl}-3-methoxymethyl-phenyl)-methanesulfonamide

Procedure

step 1—Cross coupling of 315 and 6-methyl-2-methoxy-3-pyridine boronic acid (316, CASRN 1000802-754) was carried out in accord with the procedure in step 4 of example 38 except 107 was replaced with 316 which afforded N-(4-{(E)-2-[3-tert-butyl-2-methoxy-5-(2-methoxy-6-methyl-pyridin-3-yl)-phenyl]-vinyl}-3-methoxymethyl-phenyl)-methanesulfonamide (318).

Sources & evidence

ORD record
ord-bb418001bf234ec7ba8b393bc135a3f3
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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