Methyl 5-bromopyridine-3-carboxylate → Methyl 5-[3-methyl-4-(trifluoromethoxy)phenyl]pyridine-3-carboxylate

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH3:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:18]=1[O:19][C:20]([F:23])([F:22])[F:21]>>[CH3:12][C:13]1[CH:14]=[C:15]([C:2]2[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[N:4][CH:3]=2)[CH:16]=[CH:17][C:18]=1[O:19][C:20]([F:21])([F:22])[F:23]

Participants

Reactant 2

HCID 699336Methyl 5-bromopyridine-3-carboxylate

HCID 46739138(3-Methyl-4-(trifluoromethoxy)phenyl)boronic acid

Product 1

HCID 58002517Methyl 5-[3-methyl-4-(trifluoromethoxy)phenyl]pyridine-3-carboxylate

Procedure

2.7 g (12.5 mmol) of methyl 5-bromonicotinate and 3.3 g (15.0 mmol) of [3-methyl-4-(trifluoromethoxy)phenyl]boronic acid were reacted according to the General Method 1A. Yield: 3.1 g (80% of theory)

Sources & evidence

ORD record: ord-b6eb256e09af422084beea3e367a1d1c
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119663B2

Reaction notes

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