Triacetoxyperiodinane → 2-[(4-Oxidanylidenecyclohexyl)amino]-4-(3,6,6-Trimethyl-4-Oxidanylidene-5,7-Dihydroindol-1-Yl)benzamide

HRID 900460Notes

Reaction equation

HRID 900460 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:17]=[C:16]([N:18]3[C:26]4[CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][C:22](=[O:29])[C:21]=4[C:20]([CH3:30])=[CH:19]3)[CH:15]=[CH:14][C:10]=2[C:11]([NH2:13])=[O:12])[CH2:4][CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([NH:8][C:9]2[CH:17]=[C:16]([N:18]3[C:26]4[CH2:25][C:24]([CH3:27])([CH3:28])[CH2:23][C:22](=[O:29])[C:21]=4[C:20]([CH3:30])=[CH:19]3)[CH:15]=[CH:14][C:10]=2[C:11]([NH2:13])=[O:12])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178429921HCID 178429921, compound

Product 1

HCID 118539142-[(4-Oxidanylidenecyclohexyl)amino]-4-(3,6,6-Trimethyl-4-Oxidanylidene-5,7-Dihydroindol-1-Yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound of Example 3 [2-(4-Hydroxycyclohexylamino)-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindol-1-yl)-benzamide] (150 mg, 0.366 mmol) and Dess-Martin periodinane (0.366 mmol) were dissolved in anhydrous CH2Cl2 and stirred at room temperature for one hour. The reaction mixture was concentrated and the title compound was isolated as a white solid (36.2 mg, 24% yield) after purification by column chromatography eluting with EtOAc-MeOH. LCMS m/z: (M+H)=408.3.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-fe323db4c7f345cf8ecead75d5ddf788
Source dataset
uspto-grants-2008_04
Patent number
US07358370B2

Reaction notes

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