2-Iodoxybenzoic acid → HCID 86652353, compound

HRID 340275Notes

Reaction equation

HRID 340275 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][C:15]=3[CH3:22])=[CH:7][C:6]=2[C:5]2[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:4]=2[N:3]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O.O>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([CH:20]=[O:21])=[CH:16][C:15]=3[CH3:22])=[CH:7][C:6]=2[C:5]2[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 58213531HCID 58213531, compound

Product 1

HCID 86652353HCID 86652353, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of (4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenyl)methanol (from the previous step) in DMSO was added 2-iodoxybenzoic acid (IBX, 2.5 eq). The reaction was stirred at room temperature for 3 hours before being diluted with water. Extraction with EtOAc followed by concentration gave a crude residue which was purified by chromatography (silica gel, 50-100% EtOAc in hexanes) to afford 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylbenzaldehyde.

Workup

  1. extractionExtraction with EtOAc
  2. concentrationfollowed by concentration
  3. customgave a crude residue which
  4. customwas purified by chromatography (silica gel, 50-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2339e9408ef74cf88bcac2303c394d28
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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