Water → Ethyl 3-chloro-2-methylisonicotinate

HRID 1508202Notes

Reaction equation

HRID 1508202 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][N:8]=[C:7](Cl)[C:6]=1[Cl:12])[CH3:2].[C:14]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1.O>O1CCOCC1.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>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH3:14])[C:6]=1[Cl:12])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 46311339Ethyl 2,3-dichloropyridine-4-carboxylate

Product 1

HCID 86721905Ethyl 3-chloro-2-methylisonicotinate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,3-dichloroisonicotinic acid ethyl ester (3.15 mmol), K2CO3 (4.73 mmol) and trimethylboroxine (3.15 mmol) in 4 mL dioxane was degassed with Ar. Then, tetrakis(triphenylphosphine)palladium (0.31 mmol) was added and the mixture was heated to reflux overnight. At RT, the reaction mixture was poured into water and extracted with DCM. The combined organic layers were dried over K2CO3, filtered over a pad of celite and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept/EtOAc (8/2) gives the desired product as brown oil;

Workup

  1. customwas degassed with Ar
  2. temperaturethe mixture was heated
  3. temperatureto reflux overnight
  4. extractionextracted with DCM
  5. dry with materialThe combined organic layers were dried over K2CO3
  6. filtrationfiltered over a pad of celite
  7. concentrationconcentrated in vacuo
  8. customPurification by CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-eff0175657f346fc9430896d99cce9be
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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