Diethyl Ether → HCID 57517330, compound

HRID 1629717Notes

Reaction equation

HRID 1629717 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH3:12].CC(C)([O-])C.[K+].[I:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22](I)[CH:21]=1.CCOCC>COCCOC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([I:19])[CH:21]=2)([CH3:9])[CH3:10])=[CH:4][C:3]=1[CH3:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 12270Benzene, 1,3-diiodo-HCID 23665647Potassium tert-butoxideHCID 57517329HCID 57517329, compound

Product 1

HCID 57517330HCID 57517330, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of amine INT 22 (2.8 g, 15.24 mmol) and potassium tert-butoxide (5.99 g, 53.4 mmol) in DME (25 mL) was purged with argon for 5 minutes. Then, PEPPSI-IPr® (207 mg, 0.305 mmol) and 1,3-diiodobenzene (5.03 g, 15.24 mmol) were added and the flask was closed. The mixture was stirred at room temperature over the weekend. The crude reaction mixture was treated with Et2O (50 mL) and filtered. The residue was washed with more Et2O (30 mL) and the combined filtrates were concentrated. The crude was purified by chromatography on silica gel (cyclohexane/CH2Cl2).

Workup

  1. customwas purged with argon for 5 minutes
  2. customthe flask was closed
  3. customThe crude reaction mixture
  4. filtrationfiltered
  5. washThe residue was washed with more Et2O (30 mL)
  6. concentrationthe combined filtrates were concentrated
  7. customThe crude was purified by chromatography on silica gel (cyclohexane/CH2Cl2)

Sources & evidence

ORD record
ord-a98f5baf998e49f097c9e9daff46fdf8
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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