(5-Chloro-2-methoxypyridin-4-yl)boronic acid → 5-Chloro-4-[5-chloro-2-(trifluoromethyl)phenyl]-2-methoxypyridine

HRID 56709

Reaction equation

HRID 56709 reaction equation
[Cl:1][C:2]1[C:3](B(O)O)=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.Br[C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[C:21]([F:24])([F:23])[F:22]>CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=C(C(C)C)C=1)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+]>[Cl:1][C:2]1[C:3]([C:16]2[CH:17]=[C:18]([Cl:20])[CH:19]=[CH:14][C:15]=2[C:21]([F:22])([F:23])[F:24])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 11030558(5-Chloro-2-methoxypyridin-4-yl)boronic acidHCID 202698572-Bromo-4-chloro-1-(trifluoromethyl)benzene

Product 1

HCID 1176056205-Chloro-4-[5-chloro-2-(trifluoromethyl)phenyl]-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 54751079XPhos PalladacycleCatalyst

Procedure

443 mg (2.20 mmol) of 5-chloro-2-methoxypyridin-4-ylboronic acid and 571 mg (2.20 mmol) of 2-bromo-4-chloro-1-(trifluoromethyl)benzene in the presence of XPhos precatalyst were reacted according to General Method 2B. Yield: 193 mg (purity 93%, 25% of theory)

Sources & evidence

ORD record
ord-fa6e63b98ed947ad9d7b691e79ba8e50
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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