Methyl 6-bromo-5-fluoropyridine-2-carboxylate → HCID 70655091, compound

HRID 879112Notes

Reaction equation

HRID 879112 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[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:17]=[C:16]([F:26])[C:15]=1B1OC(C)(C)C(C)(C)O1>>[F:13][C:14]1[CH:19]=[C:18]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:17]=[C:16]([F:26])[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 70654502HCID 70654502, compound

Product 1

HCID 70655091HCID 70655091, compoundYield 59%

Procedure

Method 1 was followed using methyl 6-bromo-5-fluoropicolinate (1.0 equiv.) and 2-(2,6-difluoro-4-(tetrahydro-2H-pyran-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.0 equiv.) at 100° C. for 20 min in microwave to give methyl 6-(2,6-difluoro-4-(tetrahydro-2H-pyran-4-yl)phenyl)-5-fluoropicolinate in 59% yield. LC/MS=352.2 (MH+), Rt=0.92 min.

Workup

  1. customat 100° C.
  2. customfor 20 min

Sources & evidence

ORD record
ord-2ca05702fada413e87e94400bee3f7ce
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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