2-Methylphenyl boronic acid → Methyl 6-[3-(benzyloxy)-4-(trifluoromethyl)phenyl]-5-(2-methylphenyl)pyridine-2-carboxylate

HRID 1040364Notes

Reaction equation

HRID 1040364 reaction equation
[O-]S(C(F)(F)F)(=O)=O.[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([C:27]2[N:32]=[C:31]([C:33]([O:35][CH3:36])=[O:34])[CH:30]=[CH:29][C:28]=2O)[CH:20]=[CH:21][C:22]=1[C:23]([F:26])([F:25])[F:24])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1B(O)O>>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([C:27]2[N:32]=[C:31]([C:33]([O:35][CH3:36])=[O:34])[CH:30]=[CH:29][C:28]=2[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[CH3:38])[CH:20]=[CH:21][C:22]=1[C:23]([F:24])([F:26])[F:25])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 27332672-Methylphenyl boronic acidHCID 2758875TrifluoromethanesulfonateHCID 66720930Methyl 6-[3-(benzyloxy)-4-(trifluoromethyl)phenyl]-5-hydroxypyridine-2-carboxylate

Product 1

HCID 66720868Methyl 6-[3-(benzyloxy)-4-(trifluoromethyl)phenyl]-5-(2-methylphenyl)pyridine-2-carboxylateYield 89%

Procedure

According to the triflate/Suzuki coupling steps described in examples 4.4 and 4.5 respectively, starting from 4.38 g (10.9 mmol) of methyl 6-[3-(benzyloxy)-4-(trifluoromethyl)phenyl]-5-hydroxypyridine-2-carboxylate and 1.8 g (13.1 mmol) of 2-methylphenylboronic acid, we obtain 4.63 g of methyl 6-[3-(benzyloxy)-4-(trifluoromethyl)phenyl]-5-(2-methylphenyl)pyridine-2-carboxylate in the form of a white solid.

Sources & evidence

ORD record
ord-0b213659ba4a4269897c4b10a6255c20
Source dataset
uspto-grants-2013_10
Patent number
US08552201B2

Reaction notes

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