2-Bromopyridine → HCID 69085397, compound

HRID 594222Notes

Reaction equation

HRID 594222 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:14]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:8][C:9]1[CH:14]=[C:13]([CH:12]=[C:11]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:10]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

8

Reactant 4

HCID 79732-BromopyridineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 44118784[3-Chloro-5-(methoxycarbonyl)phenyl]boronic acid

Product 1

HCID 69085397HCID 69085397, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of commercially available 2-bromopyridine (294 mg; 1.86 mmol), 3-chloro-5-(methoxycarbonyl)phenylboronic acid (400 mg; 1.86 mmol), K2CO3 (515 mg; 3.73 mmol), and PdCl2(PPh3)2 (130 mg; 0.18 mmol) in THF (4 ml) and water (4 ml) was stirred at rt, under nitrogen, for 17 h. Water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=15/1) afforded methyl 3-chloro-5-(pyridin-2-yl)benzoate as a colorless solid. LC-MS (conditions A): tR=0.79 min.; [M+H]+: 247.95 g/mol.

Workup

  1. extractionThe separated aq. layer was further extracted with AcOEt
  2. washThe mixed organic layers were washed with brine
  3. dry with materialdried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification by FC (DCM/MeOH=15/1)

Sources & evidence

ORD record
ord-51acc2e8b50849468e22a86db32060f8
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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