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2-Bromopyridine → Methyl 2-chloro-5-(pyridin-2-yl)benzoate

HRID 594219
Notes
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Reaction equation

HRID 594219 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19].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]=[CH:13][C:12]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 79732-BromopyridineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 230053344-Chloro-3-(methoxycarbonyl)benzeneboronic acid

Product 1

HCID 57422925Methyl 2-chloro-5-(pyridin-2-yl)benzoate

Reagents, catalysts & solvents 3

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 962WaterSolvent2×
HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of commercially available 2-bromopyridine (294 mg; 1.86 mmol), 4-chloro-3-(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 20 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 (heptane/AcOEt=7/3) afforded methyl 2-chloro-5-(pyridin-2-yl)benzoate as a colorless solid. LC-MS (conditions A): tR=0.65 min.; [M+H]+: 248.02 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 (heptane/AcOEt=7/3)

Sources & evidence

ORD record
ord-d5d8bed17b5b4dfebe86acafc69c115c
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242970B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes