Sodium Iodide → HCID 68782588, compound

HRID 2267118Notes

Reaction equation

HRID 2267118 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([C@@H:20](O)[CH2:21][CH2:22][C:23]4[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=4[C:25]([O:27][CH3:28])=[O:26])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.C(#N)C.[I-:37].[Na+].C[Si](C)(C)Cl>CO.C(Cl)Cl.O.C(OCC)(=O)C.C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([C@@H:20]([I:37])[CH2:21][CH2:22][C:23]4[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=4[C:25]([O:27][CH3:28])=[O:26])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

10

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 9955783Methyl 2-[(3S)-3-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate

Product 1

HCID 68782588HCID 68782588, compound

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Adding anhydrous methyl 2-[(3S)-[3-[(2E)-(7-chloro quinolin-2-yl)ethenyl]phenyl]-3-hydroxypropyl]benzoate (1) solution in organic polar solvent such as acetonitrile, THF to a solution of sodium iodide at temperature of about 10° C. to about 25° C. followed by addition of trimethylchloro silane to the mass, raising the temperature to about 35° C. to about 55° C., maintaining the reaction mass at temperature of 35° C. to 55° C. for about 10 hrs to 24 hrs, isolation, slurring the wet cake with mixture of ethyl acetate, water gives the crude iodo derivative (IV, X═I). The crude on dissolution in mixture of methylene chloride, methanol followed by washing with sodium bicarbonate solution, water, drying over dehydrating agents such as anhydrous sodium sulphate, anhydrous magnesium sulphate, removal of solvent under reduced pressure at temperature below 50° C. followed by purification with column chromatography gives the pure methyl 2-[(3S)-[3-[(2E)-(7-chloro quinolin-2-yl)ethenyl]phenyl]-3-iodopropyl]benzoate (IV, X═I).

Workup

  1. temperatureraising the temperature to about 35° C. to about 55° C.
  2. temperaturemaintaining the reaction mass at temperature of 35° C. to 55° C. for about 10 hrs to 24 hrs
  3. customgives the crude iodo derivative (IV, X═I)
  4. dissolutionThe crude on dissolution
  5. washby washing with sodium bicarbonate solution, water
  6. customdrying
  7. customsuch as anhydrous sodium sulphate, anhydrous magnesium sulphate, removal of solvent under reduced pressure at temperature below 50° C.
  8. customfollowed by purification with column chromatography

Sources & evidence

ORD record
ord-d49177c0b8704e07b24a120e54b53204
Source dataset
uspto-grants-2010_12
Patent number
US07858793B2

Reaction notes

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