2-Iodoxybenzoic acid → 1-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-phenyl]-5-(4-methoxy-benzyloxy)-4-oxo-1,4-dihydro-pyridine-2-carbaldehyde

HRID 571072Notes

Reaction equation

HRID 571072 reaction equation
[Cl:1][C:2]1[C:3]([C:11]2[CH:12]=[C:13]([N:17]3[CH:22]=[C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[C:20](=[O:33])[CH:19]=[C:18]3[CH2:34][OH:35])[CH:14]=[CH:15][CH:16]=2)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C([O-])(O)=O.[Na+].O>[Cl:1][C:2]1[C:3]([C:11]2[CH:12]=[C:13]([N:17]3[CH:22]=[C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[C:20](=[O:33])[CH:19]=[C:18]3[CH:34]=[O:35])[CH:14]=[CH:15][CH:16]=2)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 699320591-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-phenyl]-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-1H-pyridin-4-one

Product 1

HCID 866802761-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-phenyl]-5-(4-methoxy-benzyloxy)-4-oxo-1,4-dihydro-pyridine-2-carbaldehyde

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1.44 g (2.95 mmol) 1-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-phenyl]-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-1H-pyridin-4-one in 14.5 mL DMSO was added 1.67 g (5.90 mmol) o-iodoxybenzoic acid (99%). The mixture was stirred for 4 h at room temperature, then slowly diluted with 30 mL of a 1:1:1 mixture of sat. aq. sodium thiosulfate, sat. aq. NaHCO3, and water. The crude product precipitated and was collected by filtration and dried in vacuo. Purification by automated flash chromatography (40 g silica gel cartridge 0-10% MeOH/EtOAc over 30 min afforded 1-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-phenyl]-5-(4-methoxy-benzyloxy)-4-oxo-1,4-dihydro-pyridine-2-carbaldehyde. 1H NMR (300 MHz, DMSO-d□): δ 9.56 (s, 1 H); 8.36 (s, 1 H); 7.81-7.59 (m, 6 H); 7.35 (d, J=8.35 Hz, 2 H); 6.93 (d, J=8.32 Hz, 2 H); 6.87 (s, 1 H); 6.32 (d, J=3.42 Hz, 1 H); 5.00 (s, 2 H); 3.74 (s, 3 H).

Workup

  1. customThe crude product precipitated
  2. filtrationwas collected by filtration
  3. customdried in vacuo
  4. customPurification by automated flash chromatography (40 g silica gel cartridge 0-10% MeOH/EtOAc over 30 min

Sources & evidence

ORD record
ord-2b82b481b40e4e6397062b9591a10c4c
Source dataset
uspto-grants-2015_05
Patent number
US09024032B2

Reaction notes

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