Triethylamine → Methyl 5-fluoro-3-methylpyridine-2-carboxylate

HRID 1186206Notes

Reaction equation

HRID 1186206 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1.CCN(CC)CC.C[CH2:18][O:19][C:20](C)=[O:21]>CO.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:18][O:19][C:20]([C:2]1[C:7]([CH3:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1)=[O:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 248203202-Bromo-5-fluoro-3-methylpyridine

Product 1

HCID 58563046Methyl 5-fluoro-3-methylpyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-bromo-5-fluoro-3-methyl-pyridine (4.90 g) in AcOEt (100 ml) and MeOH (10 ml) was subsequently added NEt3 (5.4 ml) and 1,1′-bis(diphenylphosphino) ferrocene-palladium(II)dichloride dichloromethane adduct (490 mg) and the mixture was carbonylated at 100 bar CO and 110° C. for 20 h. The mixture was evaporated and the residue purified by chromatography on silica gel using n-heptane/AcOEt (7:1) to give the title compound (3.44 g) as a pale red solid. MS: m/z=170.1 [M+H]+.

Workup

  1. customThe mixture was evaporated
  2. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8e43165d462b4a2a8a0974b657f9cc34
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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