2-Bromo-3-chloro-5-methylpyridine → Methyl 3-chloro-2'-{4-chloro-3-[(4-methoxybenzyl)oxy]phenyl}-5-methyl-2,3'-bipyridine-6'-carboxylate

HRID 244067Notes

Reaction equation

HRID 244067 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([C:16]3[N:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][C:17]=3B3OC(C)(C)C(C)(C)O3)[CH:12]=[CH:13][C:14]=2[Cl:15])=[CH:5][CH:4]=1.Br[C:38]1[C:43]([Cl:44])=[CH:42][C:41]([CH3:45])=[CH:40][N:39]=1>>[Cl:44][C:43]1[C:38]([C:17]2[C:16]([C:11]3[CH:12]=[CH:13][C:14]([Cl:15])=[C:9]([O:8][CH2:7][C:6]4[CH:35]=[CH:36][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[CH:10]=3)=[N:21][C:20]([C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:18]=2)=[N:39][CH:40]=[C:41]([CH3:45])[CH:42]=1

Participants

3

Reactant 2

HCID 126309842-Bromo-3-chloro-5-methylpyridineHCID 66841210Methyl 6-[3-[(4-methoxybenzyl)oxy]-4-chlorophenyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate

Product 1

HCID 66840933Methyl 3-chloro-2'-{4-chloro-3-[(4-methoxybenzyl)oxy]phenyl}-5-methyl-2,3'-bipyridine-6'-carboxylateYield 64%

Procedure

The Suzuki-Myaura coupling performed between 1 g (1.96 mmol) of methyl 6-[3-[(4-methoxybenzyl)oxy]-4-chlorophenyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate and 526 mg (2.55 mmol) of 2-bromo-3-chloro-5-methylpyridine according to Example 1.6 gives 637 mg of methyl 3-chloro-2′-{4-chloro-3-[(4-methoxybenzyl)oxy]phenyl}-5-methyl-2,3′-bipyridine-6′-carboxylate in the form of an oil.

Sources & evidence

ORD record
ord-0cc0f6ddfc9d46ff8af48455b7e503a2
Source dataset
uspto-grants-2014_02
Patent number
US08653276B2

Reaction notes

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