3-(Benzyloxy)-2,6-difluorobenzeneboronic acid → Methyl 6-(3-(benzyloxy)-2,6-difluorophenyl)picolinate

HRID 2046876Notes

Reaction equation

HRID 2046876 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH2:12]([O:19][C:20]1[C:21]([F:30])=[C:22](B(O)O)[C:23]([F:26])=[CH:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([O:19][C:20]1[C:21]([F:30])=[C:22]([C:2]2[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=2)[C:23]([F:26])=[CH:24][CH:25]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 162177043-(Benzyloxy)-2,6-difluorobenzeneboronic acidHCID 16217886Methyl 6-bromopyridine-2-carboxylate

Product 1

HCID 59226396Methyl 6-(3-(benzyloxy)-2,6-difluorophenyl)picolinateYield 95%

Procedure

Method 6 was followed using methyl 6-bromopicolinate (1.0 equiv.) and 3-(benzyloxy)-2,6-difluorophenylboronic acid (2.5 equiv.) to give methyl 6-(3-(benzyloxy)-2,6-difluorophenyl)picolinate as a light yellow solid in 95% yield. LC/MS=356.2 (M+H), Rt=1.03 min.

Sources & evidence

ORD record
ord-cc513809424b46be86422f2bd30edd4c
Source dataset
uspto-grants-2013_11
Patent number
US08592455B2

Reaction notes

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