Sodium Iodide → HCID 49772437, compound

HRID 252608Notes

Reaction equation

HRID 252608 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-d699d9c9cf384f3cb51fb3dd1013c076
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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