Sodium Iodide → HCID 131724208, compound

HRID 1786820Notes

Reaction equation

HRID 1786820 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:15][C:14]3([CH:20]=[CH:19][C:18]4[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=4[O:16]3)[CH2:13][CH2:12][N:11]2[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:5]=[C:6]([F:9])[C:7]=1[OH:8].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].I[CH2:40][CH3:41]>C(OCC)(=O)C.CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:15][C:14]3([CH:20]=[CH:19][C:18]4[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=4[O:16]3)[CH2:13][CH2:12][N:11]2[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:5]=[C:6]([F:9])[C:7]=1[O:8][CH2:40][CH3:41]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 131724209HCID 131724209, compound

Product 1

HCID 131724208HCID 131724208, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To ethyl (3,5-difluoro-4-hydroxyphenyl)spiro[2H-1-benzopyran-2,4′-piperidine]-1′-acetate (350 mg), cesium carbonate (412 mg) and sodium iodide (13 mg) was added N,N-dimethylformamide (9 cm3) followed by iodoethane (1.7 mole equiv.). The resulting mixtures were heated to 65° C. with stirring for 3 h. Upon cooling, the reaction was diluted with ethyl acetate (90 cm3) then washed with water (5×35 cm3) and dried (Na2SO4). This solution of crude material was then filtered through a pad of silica before the solvent was removed in vacuo to afford the product in a homogeneous state.

Workup

  1. temperatureUpon cooling
  2. washthen washed with water (5×35 cm3)
  3. dry with materialdried (Na2SO4)
  4. filtrationThis solution of crude material was then filtered through a pad of silica before the solvent
  5. customwas removed in vacuo
  6. customto afford the product in a homogeneous state

Sources & evidence

ORD record
ord-a1a4acf497f844dd99c330c8479391ef
Source dataset
uspto-grants-2009_03
Patent number
US07507824B2

Reaction notes

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