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Dichloromethane → 3-[5-(2,3-Dichloro-phenyl)-pyridin-3-yl]-propionic acid methyl ester

HRID 2407456
Notes
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Reaction equation

HRID 2407456 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10](Br)[CH:11]=1.[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:14])[C:20]=2[Cl:21])[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27346612,3-Dichlorobenzeneboronic acidHCID 59578425Methyl 3-(5-bromopyridin-3-yl)propanoate

Product 1

HCID 595784053-[5-(2,3-Dichloro-phenyl)-pyridin-3-yl]-propionic acid methyl esterYield 51.3%

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(5-bromo-pyridin-3-yl)-propionic acid methyl ester (155 mg), 2,3-dichlorobenzeneboronic acid (142 mg, 0.744 mmol), PdCl2(dppf).CH2Cl2 adduct (48.6 mg, 0.059 mmol) and Na2CO3 (2 M, 0.929 ml, 1.859 mmol) in DMF (5 ml) was heated at 100° C. After 40 min, solvent was removed in vacuo. The residue was purified via flash column (EtOAc/Heptane=0-20-25%, v/v) to give 3-[5-(2,3-Dichloro-phenyl)-pyridin-3-yl]-propionic acid methyl ester (101 mg, 0.326 mmol, 43% yield). ESI-MS m/z: 310[M+1]+; 1H NMR (CDCl3, 400 MHz) δ 2.71 (t, J=7.6 Hz, 2H), 3.05 (t, J=7.6 Hz, 2H), 3.70 (s, 3H), 7.23 (dd, J=7.6, 1.6 Hz, 1H), 7.30 (t, J=7.6 Hz, 1H), 7.53 (dd, J=7.6, 1.6 Hz, 1H), 7.63 (s, 1H), 8.52 (s, 2H).

Workup

  1. customsolvent was removed in vacuo
  2. customThe residue was purified via flash column (EtOAc/Heptane=0-20-25%, v/v)

Sources & evidence

ORD record
ord-b0b387321a95421995b0f37a480719ac
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08809545B2

Reaction notes

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