Potassium Carbonate → HCID 57557415, compound

HRID 1522829Notes

Reaction equation

HRID 1522829 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=1)[C:9]([OH:15])=[N:8][CH:7]=[CH:6]2.I[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.O.CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=1)[C:9](=[O:15])[N:8]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH:7]=[CH:6]2

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 696764-IodoanisoleHCID 145742L-ProlineHCID 178493401HCID 178493401, compound

Product 1

HCID 57557415HCID 57557415, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

6,8-Dimethoxyisoquinolin-1-ol (1.59 g, 7.75 mmol), 4-iodoanisole (2.72, 11.62 mmol), copper(I) iodide (0.30 g, 1.55 mmol), L-proline (0.36 g, 3.10 mmol) and anhydrous potassium carbonate (2.14 g, 15.50 mmol) were placed in a dry 250 mL three-necked round-bottomed flask fitted with a stirring bar and reflux condenser. The system was vacuumed and refilled with dry argon. Then, anhydrous methyl sulfoxide (50 mL) was added via a syringe under argon atmosphere. The reaction solution was stirred and heated to 120° C. for 20 h. Water (20 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (5×20 mL). The extracts were combined, washed with brine (3×10 mL) and dried over anhydrous MgSO4 followed by filtration and concentration to give a yellow residue. The yellow residue was purified by flash column chromatography (silica-gel, EtOAc) to give a pale-yellow solid product, 2.12 g, 88.0% yield. MS: m/z 312.9 [M+H]+. 1H NMR (DMSO-d6, 300 MHz): δ 7.31-7.26 (m, 3H), 7.02 (d, 2H, J=8.7 Hz), 6.71 (d, 1H, J=2.4 Hz), 6.54 (d, 1H, J=2.4 Hz), 6.45 (d, 1H, J=7.8 Hz), 3.87 (s, 3H), 3.81 (s, 3H), 3.79 (s, 3H).

Workup

  1. customfitted with a stirring bar
  2. temperaturereflux condenser
  3. additionrefilled with dry argon
  4. customto quench
  5. customthe reaction
  6. extractionThe mixture was extracted with ethyl acetate (5×20 mL)
  7. washwashed with brine (3×10 mL)
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfollowed by filtration and concentration
  10. customto give a yellow residue
  11. customThe yellow residue was purified by flash column chromatography (silica-gel, EtOAc)
  12. customto give a pale-yellow solid product, 2.12 g, 88.0% yield

Sources & evidence

ORD record
ord-db0bb3adccbd47d78c091b6669641165
Source dataset
uspto-grants-2015_07
Patent number
US09078888B2

Reaction notes

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