Methyl 6-bromo-5-fluoropyridine-2-carboxylate → methyl 6-(2,6-difluoro-4-(4-hydroxytetrahydro-2H-pyran-4-yl)phenyl)-5-fluoropicolinate

HRID 705202Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[F:12].[F:13][C:14]1[CH:15]=[C:16]([C:30]2([OH:36])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:17]=[C:18]([F:29])[C:19]=1B1OC(C)(C)C(C)(C)O1>>[F:29][C:18]1[CH:17]=[C:16]([C:30]2([OH:36])[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)[CH:15]=[C:14]([F:13])[C:19]=1[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[F:12]

Participants

Reactant 2

HCID 46311204Methyl 6-bromo-5-fluoropyridine-2-carboxylate

HCID 70654776HCID 70654776, compound

Product 1

HCID 70655152methyl 6-(2,6-difluoro-4-(4-hydroxytetrahydro-2H-pyran-4-yl)phenyl)-5-fluoropicolinateYield 72%

Procedure

Method 1 was followed using methyl 6-bromo-5-fluoropicolinate (1.0 equiv.) and 4-(3,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H-pyran-4-ol (1.8 equiv.) at to give methyl 6-(2,6-difluoro-4-(4-hydroxytetrahydro-2H-pyran-4-yl)phenyl)-5-fluoropicolinate in 72% yield. LC/MS=368.0 (MH+), Rt=0.75 min.

Sources & evidence

ORD record: ord-f73cc271755d428280e37cef97a85ad6
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173883B2

Reaction notes

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