Cyanogen Bromide → HCID 59300932, compound

HRID 2235457Notes

Reaction equation

HRID 2235457 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][CH2:13][CH3:14])[C:6](=[O:15])[C:5]2([CH3:17])[CH3:16].Br[C:19]#[N:20].C(Cl)Cl.CO>O.C1COCC1>[NH2:20][C:19]1[NH:1][C:2]2=[CH:3][C:4]3[C:5]([CH3:16])([CH3:17])[C:6](=[O:15])[N:7]([CH2:12][CH2:13][CH3:14])[C:8]=3[CH:9]=[C:10]2[N:11]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 21226129Dichloromethane methanolHCID 67425905HCID 67425905, compound

Product 1

HCID 59300932HCID 59300932, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Analogously to general procedure (III) 5,6-diamino-3,3-dimethyl-1-propyl-1,3-dihydro-indol-2-one (1.52 g) is cyclized using BrCN (3 M; 2.4 ml; 7.2 mmol) at RT in water (5 ml) and THF (13 ml). After aqueous work-up and flash chromatography on silica gel eluting with CH2Cl2/MeOH (15:1) the desired compound (1.56 g) is obtained.

Workup

  1. customat RT

Sources & evidence

ORD record
ord-045752b09d3e4e66885f08236390baa4
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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