Sodium Iodide → HCID 49772437, compound

HRID 506121Notes

Reaction equation

HRID 506121 reaction equation
[CH:1]([O:4][C:5](=[O:33])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH:29]3[CH2:32][CH2:31][CH2:30]3)[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24][CH2:25][CH2:26][CH2:27]Cl)[CH:16]=3)=[CH:9][CH:8]=1)([CH3:3])[CH3:2].[I-].[Na+].[Na].[NH:37]1[CH:41]=[N:40][CH:39]=[N:38]1>CC#N>[CH:1]([O:4][C:5](=[O:33])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH:29]3[CH2:32][CH2:31][CH2:30]3)[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24][CH2:25][CH2:26][CH2:27][N:37]2[CH:41]=[N:40][CH:39]=[N:38]2)[CH:16]=3)=[CH:9][CH:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 92571H-1,2,4-TriazoleHCID 5360545SodiumHCID 59425759HCID 59425759, compound

Product 1

HCID 49772437HCID 49772437, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of {4-[6-(3-chloro-propoxy)-3-cyano-1-cyclobutyl-1H-indol-2-yl]-phenyl}-carbamic acid isopropyl ester (37 mg, 0.08 mmol) in CH3CN (1 mL) is added sodium iodide (71 mg, 0.48 mmol). The resulting mixture is stirred at reflux temperature overnight. The solvent is then evaporated and the residue is diluted with anhydrous DMF (1 mL) and then treated with the sodium salt of 1,2,4-triazole (0.16 mmol) at room temperature overnight. The solvent is removed under reduced pressure and the residue is diluted with ethyl acetate and then washed with water. The organic layer is concentrated and triturated with hexane and the precipitate is collected by filtration and washed well with 50% ethyl acetate in hexane and dried in vacuo to afford {4-[3-cyano-1-cyclobutyl-6-(3-[1,2,4]triazol-1-yl-propoxy)-1H-indol-2-yl]-phenyl}-carbamic acid isopropyl ester, compound 1255 (31 mg, 78%).

Workup

  1. temperatureat reflux temperature overnight
  2. customThe solvent is then evaporated
  3. additionthe residue is diluted with anhydrous DMF (1 mL)
  4. customThe solvent is removed under reduced pressure
  5. additionthe residue is diluted with ethyl acetate
  6. washwashed with water
  7. concentrationThe organic layer is concentrated
  8. customtriturated with hexane
  9. filtrationthe precipitate is collected by filtration
  10. washwashed well with 50% ethyl acetate in hexane
  11. customdried in vacuo

Sources & evidence

ORD record
ord-4382271990524d7bab90fa672f77b2b3
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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