Ethyl Acetate → HCID 86647437, compound

HRID 2071164Notes

Reaction equation

HRID 2071164 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]=[O:13])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1B(O)O.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O.C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:12]([C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([C:15]2[O:14][CH:18]=[CH:17][CH:16]=2)[N:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[O:13]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 722138911006598-63-5

Product 1

HCID 86647437HCID 86647437, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a degassed mixture of 205 mg (1.027 mmol) of methyl 2-chloro-6-formylisonicotinate, 183 mg (1.64 mmol) of 2-furanboronic acid, and 316 mg (2.98 mmol) of Na2CO3 in 2 mL of H2O and 4 mL of THF was added 263 mg (0.227 mmol) of Pd(PPh3)4. The mixture was stirred at 55° C. for 14 h, and EtOAc and H2O were added. The aqueous layer was extracted with EtOAc, and the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (10% EtOAc/hexanes) provided methyl 2-formyl-6-(furan-2-yl)isonicotinate as a yellow solid (101 mg) in 43% yield. The desired 6-(furan-2-yl)-4-(methoxycarbonyl)picolinic acid was synthesized from the aldehyde (methyl 2-formyl-6-(furan-2-yl)isonicotinate) following the general procedures as described herein.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washthe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash silica gel chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5489431e47204a948ad390b2676b3c2c
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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