Potassium Carbonate → HCID 57557417, compound

HRID 1522825Notes

Reaction equation

HRID 1522825 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([OH:13])=[N:8][CH:7]=[CH:6]2.I[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=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](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH:7]=[CH:6]2

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 696764-IodoanisoleHCID 145742L-ProlineHCID 178487746HCID 178487746, compound

Product 1

HCID 57557417HCID 57557417, compoundYield 90.3%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
130 °C

Procedure

6-Methoxyisoquinoline-1-ol (2.00 g, 11.42 mmol), 4-iodoanisole (4.01 g, 17.13 mmol), copper (1) iodide (0.44 g, 2.28 mmol). L-proline (0.53 g, 4.57 mmol) and anhydrous potassium carbonate (3.16 g, 22.84 mmol) were placed in a dry 250 mL three-necked round-bottomed flask fitted with a stirring bar and reflux condenser. The reaction flask was vacuumed and refilled with dry argon. 50 mL of anhydrous methyl sulfoxide was added via syringe. The reaction mixture was stirred and heated to 130° C. for 20 hours. 50 mL of water was added to quench the reaction, and yellow solid precipitated out. The pale-yellow solid was filtered, washed with water (2×20 mL) and dried in air. This pale-yellow solid was purified by flash column chromatography (silica gel, ethyl acetate) to give a pale-yellow solid product, 2.90 g, 90.3% yield. MS: 282.2 [M+H]+. 1H NMR (DMSO-d6, 300 MHz): δ 8.14 (d, 1H, J=8.7 Hz), 7.39-7.34 (m, 3H), 7.19 (d, 1H, J=2.4 Hz), 7.13-7.03 (m, 3H), 6.62 (dd, 1H, J=7.5 Hz), 3.89 (s, 3H), 3.81 (s, 3H).

Workup

  1. customfitted with a stirring bar
  2. temperaturereflux condenser
  3. additionrefilled with dry argon
  4. customto quench
  5. customthe reaction, and yellow solid
  6. customprecipitated out
  7. filtrationThe pale-yellow solid was filtered
  8. washwashed with water (2×20 mL)
  9. customdried in air
  10. customThis pale-yellow solid was purified by flash column chromatography (silica gel, ethyl acetate)
  11. customto give a pale-yellow solid product, 2.90 g, 90.3% yield

Sources & evidence

ORD record
ord-b61eb4b1819247869b96193268474261
Source dataset
uspto-grants-2015_07
Patent number
US09078888B2

Reaction notes

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