Sodium Iodide → 1-{4-[(4-cyanobenzyl)oxy]phenyl}-1H-indole

HRID 854495Notes

Reaction equation

HRID 854495 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=1.[Na+].[I-].C(O)C(N)(CO)CO>CN(C=O)C>[C:31]([C:28]1[CH:29]=[CH:30][C:25]([CH2:24][O:1][C:2]2[CH:7]=[CH:6][C:5]([N:8]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:10]=[CH:9]3)=[CH:4][CH:3]=2)=[CH:26][CH:27]=1)#[N:32]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6503Tris(hydroxymethyl)aminomethaneHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 166556721-(4-hydroxyphenyl)-1H-indole

Product 1

HCID 685459691-{4-[(4-cyanobenzyl)oxy]phenyl}-1H-indoleYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.038 g (0.18 mmol) 1-(4-hydroxyphenyl)-1H-indole in 1.2 ml DMF was added 0.05 g (0.38 mmol) K2CO3 and the slurry was mixed for 30 min. 59 mg (0.3 mmol) α-bromo-p-tolunitrile and 0.01 g (66 μmol) NaI was added and the slurry was mixed at 60° C. for 4 hr. The solution was allowed to cool and an additional 2 ml DMF was added, followed by 0.10 g PS-Trisamine scavenger reagent (Argonaut Technologies, San Carlos, Calif.). The slurry was mixed at 60° C. for a further 3 hr and allowed to cool. The reaction was filtered and the solution was concentrated to afford 0.045 g 1-{4-[(4-cyanobenzyl)oxy]phenyl}-1H-indole as an oil.

Workup

  1. additionthe slurry was mixed for 30 min
  2. additionthe slurry was mixed at 60° C. for 4 hr
  3. temperatureto cool
  4. additionThe slurry was mixed at 60° C. for a further 3 hr
  5. temperatureto cool
  6. filtrationThe reaction was filtered
  7. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-a1d918ed61064565b675a62c7ff35f08
Source dataset
uspto-grants-2007_08
Patent number
US07259182B2

Reaction notes

Loading…