Methyl 6-bromo-5-hydroxy-2-pyridinecarboxylate → Methyl 6-[3-(benzyloxy)-4-(trifluoromethyl)phenyl]-5-hydroxypyridine-2-carboxylate

HRID 1040363Notes

Reaction equation

HRID 1040363 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][C:14]=1[C:15]([F:18])([F:17])[F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:23]1[N:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:25][C:24]=1[OH:33]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:23]2[N:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:25][C:24]=2[OH:33])[CH:12]=[CH:13][C:14]=1[C:15]([F:18])([F:17])[F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 15281236Methyl 6-bromo-5-hydroxy-2-pyridinecarboxylateHCID 567766183-(Benzyloxy)-4-(trifluoromethyl)phenylboronic acid

Product 1

HCID 66720930Methyl 6-[3-(benzyloxy)-4-(trifluoromethyl)phenyl]-5-hydroxypyridine-2-carboxylateYield 65%

Procedure

According to the method described in example 4.3, starting from 4.95 g (16.7 mmol) of [3-(benzyloxy)-4-(trifluoromethyl)phenyl]boronic acid and 3.88 g (16.72 mmol) of methyl 6-bromo-5-hydroxypyridine-2-carboxylate, we obtain 4.38 g of methyl 6-[3-(benzyloxy)-4-(trifluoromethyl)phenyl]-5-hydroxypyridine-2-carboxylate in the form of a white solid.

Sources & evidence

ORD record
ord-de5375f1ae1747338adddb62cd15e83b
Source dataset
uspto-grants-2013_10
Patent number
US08552201B2

Reaction notes

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