Cyanogen Bromide → 2-Amino-5-ethyl-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

HRID 2235456Notes

Reaction equation

HRID 2235456 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[N:7]([CH2:12][CH3:13])[C:6](=[O:14])[C:5]2([CH3:16])[CH3:15].Br[C:18]#[N:19]>O.C1COCC1>[NH2:19][C:18]1[NH:1][C:2]2=[CH:3][C:4]3[C:5]([CH3:15])([CH3:16])[C:6](=[O:14])[N:7]([CH2:12][CH3:13])[C:8]=3[CH:9]=[C:10]2[N:11]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 674257515,6-Diamino-1-ethyl-3,3-dimethyl-1,3-dihydro-indol-2-one

Product 1

HCID 593007322-Amino-5-ethyl-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Analogously to general procedure (III) 5,6-diamino-1-ethyl-3,3-dimethyl-1,3-dihydro-indol-2-one (1.32 g) is cyclized using BrCN (3 M; 2.2 ml; 6.6 mmol) at RT in water (5 ml) and THF (13 ml). After aqueous work-up and re-crystallization from EtOAc the desired compound (1.03 g) is obtained as a solid.

Workup

  1. customat RT
  2. customAfter aqueous work-up and re-crystallization from EtOAc the desired compound (1.03 g)
  3. customis obtained as a solid

Sources & evidence

ORD record
ord-38ca61884d1f4b1abace6dc42818a817
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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