Potassium Iodide → HCID 59004671, compound

HRID 1668456Notes

Reaction equation

HRID 1668456 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>ClCCl>[N+:14]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][CH2:3][CH2:2][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)[CH:6]=[CH:7]2)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 11172472HCID 11172472, compound

Product 1

HCID 59004671HCID 59004671, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
81 °C

Procedure

To a small reaction vial containing a magnetic stirbar was added compound 38 (155 mg, 0.649 mmol), potassium iodide (1.078 g, 6.49 mmol) and potassium carbonate (898.0 mg, 6.49 mmol). The vial was sealed and purged with argon. Anhydrous acetonitrile (4 mL) was added through the septum, followed by morpholine (0.57 mL, 6.54 mmol). The vial was placed in the heating block and stirred at 81° C. for 68 hours. The reaction was cooled to room temperature. The non-homogenous reaction was diluted with dichloromethane (5 mL) and filtered through celite. Additional dichloromethane (10 mL) followed by methanol (5 mL) was used to wash the celite plug. The filtrate was concentrated on the rotary evaporator and dried further under high vacuum. The product was purified using silica gel column chromatography (2M NH3 in methanol:CH2Cl2, 5:95) to obtain compound 39 (190 mg, 100%) as a yellow oil. 1H NMR (CDCl3) δ 8.59 (d, J=2.1 Hz, 1H), 8.11 (dd, J=2.7, 9.0 Hz, 1H), 7.42 (d, J=9.0 Hz, 1H), 7.28 (d, J=3.3 Hz, 1H), 6.69 (d, J=3.0 Hz, 1H), 4.30 (t, J=6.3 Hz, 2H), 3.75 (brs, 4H), 2.41 (brs, 4H), 2.27 (brs, 2H), 2.04 (brs, 2H); ESI-MS (m/z, %): 290 (M+1, 100).

Workup

  1. additionTo a small reaction vial containing a magnetic stirbar
  2. customThe vial was sealed
  3. custompurged with argon
  4. additionAnhydrous acetonitrile (4 mL) was added through the septum
  5. temperatureThe reaction was cooled to room temperature
  6. customThe non-homogenous reaction
  7. filtrationfiltered through celite
  8. washto wash the celite plug
  9. concentrationThe filtrate was concentrated on the rotary evaporator
  10. customdried further under high vacuum
  11. customThe product was purified

Sources & evidence

ORD record
ord-5a68092e7b3747299fb9b0937e2f4576
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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