Cesium carbonate → HCID 58093326, compound

HRID 474997Notes

Reaction equation

HRID 474997 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[CH:7]=[C:6]([O:15][CH2:14][C:13]2[CH:16]=[CH:17][C:10]([Cl:9])=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 133974-Chlorobenzyl alcoholHCID 15165112-Chloro-4-iodopyridine

Product 1

HCID 58093326HCID 58093326, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 2-chloro-4-iodopyridine (5.0 g, 21 mmol), 4-chlorobenzyl alcohol (3.3 g, 23 mmol), cesium carbonate (8.9 g, 27 mmol), CuI (4.0 g, 21 mmol) and phenanthronine (0.76 g, 4.2 mmol) in toluene (20.0 mL) was purged with nitrogen for 10 min. The reaction mixture was heated at 105° C. overnight and then cooled and diluted with EtOAc. The resulting solution was washed with brine, passed through a pad of celite and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (hexanes/EtOAc 100% to 70%) to give the title compound (3.0 g, 56%): 1H NMR (500 MHz, CDCl3) δ 8.21 (d, J=6.0 Hz, 1H), 7.39 (d, J=8.5 Hz, 2H), 7.32 (d, J=8.5 Hz, 2H), 6.90 (d, J=2.0 Hz, 1H), 6.80 (dd, J=6.0, 2.0 Hz, 1H), 4.07 (s, 2H).

Workup

  1. customwas purged with nitrogen for 10 min
  2. temperaturecooled
  3. additiondiluted with EtOAc
  4. washThe resulting solution was washed with brine
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by flash column chromatography (hexanes/EtOAc 100% to 70%)

Sources & evidence

ORD record
ord-5ade12819ee84b9a95f437e18ce96399
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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