(5-(2-(4-Chlorophenyl)-1,3-dioxolan-2-yl)-2-(methylamino)pyridin-3-yl)(3-methoxyphenyl)methanol → (5-(2-(4-Chlorophenyl)-1,3-dioxolan-2-yl)-2-(methylamino)pyridin-3-yl)(3-methoxyphenyl)methanone

HRID 1799173Notes

Reaction equation

HRID 1799173 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([C:24]3[CH:25]=[C:26]([CH:32]([C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=4)[OH:33])[C:27]([NH:30][CH3:31])=[N:28][CH:29]=3)[O:23][CH2:22][CH2:21][O:20]2)=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([C:24]3[CH:25]=[C:26]([C:32]([C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=4)=[O:33])[C:27]([NH:30][CH3:31])=[N:28][CH:29]=3)[O:20][CH2:21][CH2:22][O:23]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 68664562(5-(2-(4-Chlorophenyl)-1,3-dioxolan-2-yl)-2-(methylamino)pyridin-3-yl)(3-methoxyphenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 68665640(5-(2-(4-Chlorophenyl)-1,3-dioxolan-2-yl)-2-(methylamino)pyridin-3-yl)(3-methoxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PCC (21.19 g, 98.58 mmol) was added to a solution of compound F (28 g, 65.72 mmol) in DCM (550 mL). The mixture was stirred at RT overnight and filtered through a pad of celite. The filtrate was concentrated and purified by column chromatography to obtain 16 g (46%, 2 steps) of compound G.

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-019219fe0e29453bbce1eeecc015ef4c
Source dataset
uspto-grants-2013_01
Patent number
US08343996B2

Reaction notes

Loading…