Methyl 6-bromo-5-fluoropyridine-2-carboxylate → Methyl 6-(2,6-difluoro-4-(oxetan-3-yl)phenyl)-5-fluoropicolinate

HRID 879127Notes

Reaction equation

HRID 879127 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:19]=[C:18]([CH:20]2[CH2:23][O:22][CH2:21]2)[CH:17]=[C:16]([F:24])[C:15]=1B1OC(C)(C)C(C)(C)O1>>[F:13][C:14]1[CH:19]=[C:18]([CH:20]2[CH2:23][O:22][CH2:21]2)[CH:17]=[C:16]([F:24])[C:15]=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

3

Reactant 2

HCID 46311204Methyl 6-bromo-5-fluoropyridine-2-carboxylateHCID 706553382-(2,6-Difluoro-4-(oxetan-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 70655142Methyl 6-(2,6-difluoro-4-(oxetan-3-yl)phenyl)-5-fluoropicolinateYield 47%

Procedure

Method 1 was followed using methyl 6-bromo-5-fluoropicolinate (1.2 equiv.) and 2-(2,6-difluoro-4-(oxetan-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.0 equiv.) at 80° C. for 15 min in microwave to give methyl 6-(2,6-difluoro-4-(oxetan-3-yl)phenyl)-5-fluoropicolinate in 47% yield. LC/MS=324.0 (MH+), Rt=0.75 min.

Workup

  1. customat 80° C.
  2. customfor 15 min

Sources & evidence

ORD record
ord-a5dd75987cd6440d9d3d02a5f0fd5557
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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