[3-Tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-(2-chloro-pyridin-4-yl)-methanol → [3-Tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-(2-chloro-pyridin-4-yl)-methanone

HRID 2390801Notes

Reaction equation

HRID 2390801 reaction equation
[C:1]([C:5]1[C:6]([O:28][CH3:29])=[C:7]([CH:19]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[CH:22]=2)[OH:20])[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[C:1]([C:5]1[C:6]([O:28][CH3:29])=[C:7]([C:19]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[CH:22]=2)=[O:20])[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86638338[3-Tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-(2-chloro-pyridin-4-yl)-methanol

Product 1

HCID 86638337[3-Tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-(2-chloro-pyridin-4-yl)-methanoneYield 86%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

step 2—To a solution of 40 (124 mg, 0.301 mmol) in DCM (10 mL) at RT was added MnO2 (528 mg, 6.073 mmol). The reaction mixture was vigorously stirred at RT overnight then the solid was filtered through a pad of CELITE. The filtrate was concentrated and the crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (5 to 10% EtOAc) to afford 106 mg (86%) of [3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-(2-chloro-pyridin-4-yl)-methanone (42) as a colorless oil.

Workup

  1. filtrationthe solid was filtered through a pad of CELITE
  2. concentrationThe filtrate was concentrated
  3. customthe crude residue was purified by SiO2 chromatography
  4. washeluting with an EtOAc/hexane gradient (5 to 10% EtOAc)

Sources & evidence

ORD record
ord-3e9f15464c294c16a4ba4b68066d6e03
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

Loading…