Iodoethane → HCID 117701588, compound

HRID 1507433Notes

Reaction equation

HRID 1507433 reaction equation
Cl.[OH:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7](=[O:20])[C:8]([CH3:19])=[C:9]([C@H:14]3[CH2:18][CH2:17][CH2:16][NH:15]3)[O:10]2)=[CH:5][CH:4]=1.N1C(C)=CC=C[C:22]=1[CH3:28].ICC.[C:32](Cl)(=[O:34])[CH3:33]>CN(C)C=O>[C:32]([O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7](=[O:20])[C:8]([CH3:19])=[C:9]([C@H:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH2:22][CH3:28])[O:10]2)=[CH:5][CH:4]=1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 6367Acetyl chlorideHCID 79372,6-Lutidine2×HCID 117701579HCID 117701579, compound

Product 1

HCID 117701588HCID 117701588, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (suspension) of 7-hydroxy-3,8-dimethyl-2-[(2R)-pyrrolidin-2-yl]-4H-chromen-4-one hydrochloride (78 mg, 0.30 mmol) obtained in Example 2-3 and 2,6-lutidine (52 μL, 0.45 mmol) in dimethylformamide (1.5 mL), iodoethane (31 μL, 0.39 mmol) was added dropwise under cooling with ice, and then the mixture was brought back to room temperature and stirred for 6.5 hours. 2,6-Lutidine (105 μL, 0.90 mmol) was added to the reaction solution, and the mixture was cooled with ice again. Then, acetyl chloride (43 μL, 0.60 mmol) was added dropwise thereto, and the mixture was brought back to room temperature and stirred overnight. The reaction solution was concentrated, and then a saturated aqueous solution of sodium bicarbonate was added to the obtained residue, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0→90/10) to obtain 58 mg of the title compound (yield: 59%).

Workup

  1. temperatureunder cooling with ice
  2. customwas brought back to room temperature
  3. temperaturethe mixture was cooled with ice again
  4. customwas brought back to room temperature
  5. stirringstirred overnight
  6. concentrationThe reaction solution was concentrated
  7. additiona saturated aqueous solution of sodium bicarbonate was added to the obtained residue
  8. extractionfollowed by extraction with ethyl acetate
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. filtrationThe desiccant was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0→90/10)

Sources & evidence

ORD record
ord-a288f618a2a54b7d8d0e689664faad50
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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