2,2'-Bipyridine → 1-cyclopropyl-4-iodopyridin-2(1H)-one

HRID 470548Notes

Reaction equation

HRID 470548 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.C1C=CN=C(C2C=[CH:17][CH:18]=[CH:19]N=2)C=1.C1(B(O)O)CC1.C([O-])([O-])=O.[Na+].[Na+]>ClC(Cl)C.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH:17]1([N:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][C:4]2=[O:8])[CH2:18][CH2:19]1

Participants

7

Reactant 4

HCID 14742,2'-BipyridineHCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 205825354-Iodo-1,2-dihydropyridin-2-one

Product 1

HCID 591903761-cyclopropyl-4-iodopyridin-2(1H)-oneYield 81%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-iodopyridin-2(1H)-one (0.2425 g, 1.10 mmol, 1.0 equiv), Cu(OAc)2 (0.2146 g, 1.18 mmol, 1.07 equiv), bipyridine (0.1832 g, 1.17 mmol, 1.07 equiv), cyclopropylboronic acid (0.2122 g, 2.47 mmol, 2.25 equiv) and Na2CO3 (0.2638 g, 2.49 mmol, 2.27 equiv) in dichloroethane (10 mL) was stirred at 70° C. for 18 h. The reaction mixture was quenched with satd aq NH4Cl, diluted with CH2Cl2, and dried over Na2SO4. After the solvent was removed under reduced pressure, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford 0.2309 g (81%) of 1-cyclopropyl-4-iodopyridin-2(1H)-one. Step 2

Workup

  1. customThe reaction mixture was quenched with satd aq NH4Cl
  2. additiondiluted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. customAfter the solvent was removed under reduced pressure
  5. customthe residue was purified by chromatography on silica gel
  6. washeluted with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-0782ef9a29664f81b80e9d290a6e2e49
Source dataset
uspto-grants-2014_01
Patent number
US08629138B2

Reaction notes

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