Methyl 6-bromo-5-fluoropyridine-2-carboxylate → HCID 66652608, compound

HRID 879106Notes

Reaction equation

HRID 879106 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]([O:20][CH2:21][CH2:22][O:23][CH3:24])[CH:17]=[C:16]([F:25])[C:15]=1B1OC(C)(C)C(C)(C)O1>>[F:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][O:23][CH3:24])[CH:17]=[C:16]([F:25])[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 66652582HCID 66652582, compound

Product 1

HCID 66652608HCID 66652608, compoundYield 95%

Procedure

Method 1 was followed using methyl 6-bromo-5-fluoropicolinate (1.0 equiv.) and 2-(2,6-difluoro-4-(2-methoxyethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.75 equiv.) at 80° C. for 1 hour to give methyl 6-(2,6-difluoro-4-(2-methoxyethoxy)phenyl)-5-fluoropicolinate in 95% yield. LC/MS=341.9 (M+H), Rt=0.89 min.

Workup

  1. customat 80° C.
  2. customfor 1 hour

Sources & evidence

ORD record
ord-da7640724da445919b2309e00780e8e0
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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