4-Iodophenol → HCID 24829683, compound

HRID 2191084Notes

Reaction equation

HRID 2191084 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:18][C:6]2[C:7]([C:16]#[CH:17])=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[C:4](=[O:19])[CH2:3]1.I[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>C(NC(C)C)(C)C.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.[Cu]I>[CH3:1][C:2]1([CH3:20])[CH2:18][C:6]2[C:7]([C:16]#[C:17][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[C:4](=[O:19])[CH2:3]1

Participants

6

Reactant 2

HCID 108944-IodophenolHCID 24829520HCID 24829520, compound

Product 1

HCID 24829683HCID 24829683, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 7912DiisopropylamineSolvent

Procedure

To a stirred solution of Example 38 (0.10 g, 0.35 mmol) and 4-iodophenol (0.11 g, 0.52 mmol) in diisopropylamine (7 mL) at 60° C. was added Pd(PPh3)2Cl2 (0.02 g, 0.03 mmol) followed by CuI (0.01 g, 0.05 mmol). After stirring for 50 minutes, the reaction mixture was concentrated in vacuo and the resulting residue was diluted with EtOAc (25 mL). The organics were then washed with sat. aqueous NaHCO3 (10 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 3:1 EtOAc/hexanes) gave the title compound (0.11 g, 85%) as an off-white powder. δH (DMSO-d6) 9.89 (1H, br. s), 7.31 (2H, d, J 8.2 Hz), 6.79 (2H, d, J 8.2 Hz), 3.78 (4H, m), 3.68 (4H, m), 2.67 (2H, s), 2.35 (2H, s), 1.06 (6H, s). LCMS (ES−) 380.4 (M−H)−.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionthe resulting residue was diluted with EtOAc (25 mL)
  3. washThe organics were then washed with sat. aqueous NaHCO3 (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (SiO2, 3:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-a4d4caef470e47e597e9c93dd4986ee7
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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