Triacetoxyperiodinane → HCID 178429338, compound

HRID 2235436Notes

Reaction equation

HRID 2235436 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[CH:12]=[C:11]3[NH:14][C:15]([NH:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:16][C:10]3=[CH:9][C:8]=2[C:7]([CH3:27])([CH3:26])[C:6]1=[O:28].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:26][C:7]1([CH3:27])[C:8]2[CH:9]=[C:10]3[N:16]=[C:15]([NH:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[NH:14][C:11]3=[CH:12][C:13]=2[N:5]([CH2:4][CH2:3][CH:2]=[O:1])[C:6]1=[O:28]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178429339HCID 178429339, compound

Product 1

HCID 178429338HCID 178429338, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[5-(3-hydroxy-propyl)-7,7-dimethyl-6-oxo-3,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl]-benzamide (1.12 g) in CH2Cl2 (10 ml) is added Dess Martin reagent (3.5 g; 8.25 mmol) and the mixture is stirred at RT for 4 h. After evaporation to dryness the crude material is purified by flash chromatography on Alox B eluting with CH2Cl2/MeOH gradient to give N-[7,7-dimethyl-6-oxo-5-(3-oxo-propyl)-3,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl]-benzamide (0.42 g).

Workup

  1. customAfter evaporation to dryness the crude material
  2. customis purified by flash chromatography on Alox B
  3. washeluting with CH2Cl2/MeOH gradient

Sources & evidence

ORD record
ord-f32ff435b42c4ecf9cd8015cb4b7f369
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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