Dichloromethane → Methyl 2-(5-(2,3-dichlorophenyl)pyridin-3-yl)cyclopropanecarboxylate

HRID 391348Notes

Reaction equation

HRID 391348 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:13]1[CH:14]=[C:15]([CH:19]2[CH2:21][CH:20]2[C:22]([O:24][CH3:25])=[O:23])[CH:16]=[N:17][CH:18]=1.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]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[C:15]([CH:19]2[CH2:21][CH:20]2[C:22]([O:24][CH3:25])=[O:23])[CH:16]=[N:17][CH:18]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27346612,3-Dichlorobenzeneboronic acidHCID 59578427Methyl 2-(5-bromopyridin-3-yl)cyclopropanecarboxylate

Product 1

HCID 59578384Methyl 2-(5-(2,3-dichlorophenyl)pyridin-3-yl)cyclopropanecarboxylateYield 74.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,3-dichlorophenylboronic acid (279 mg, 1.464 mmol), methyl 2-(5-bromopyridin-3-yl)cyclopropanecarboxylate (357 mg, 1.394 mmol), PdCl2(dppf).CH2Cl2 adduct (114 mg, 0.139 mmol) and Na2CO3 (2 M in water, 1.743 ml, 3.49 mmol) in DMF (7 ml) was heated at 100° C. under nitrogen atmosphere. After 1 h, the solvent was removed under vacuo. The residue was purified by flash column (EtOAc/Heptane=0-25%, v/v) to give methyl 2-(5-(2,3-dichlorophenyl)pyridin-3-yl)cyclopropanecarboxylate (335 mg, 1.040 mmol, 74% yield). ESI-MS m/z: 322 [M+1]+; 1H NMR (CDCl3, 400 MHz) 1.38-1.41 (m, 1H), 1.68-1.73 (m, 1H), 1.97-2.01 (m, 1H), 2.58-2.63 (m, 1H), 3.75 (s, 3H), 7.21 (dd, J=7.6, 1.2 Hz, 1H), 7.30 (t, J=7.6 Hz, 1H), 7.43 (bs, 1H), 7.53 (dd, J=7.6, 1.2 Hz, 1H), 8.48 (d, J=1.6 Hz, 1H), 8.50 (d, J=1.6 Hz, 1H),

Workup

  1. customthe solvent was removed under vacuo
  2. customThe residue was purified by flash column (EtOAc/Heptane=0-25%, v/v)

Sources & evidence

ORD record
ord-d776c9ba74e642fba110b4b4f4a19982
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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