Cesium carbonate → HCID 66813038, compound

HRID 333830Notes

Reaction equation

HRID 333830 reaction equation
Br[C:2]1[C:3]([CH3:10])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:17]([C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)(=[O:20])[CH2:18][CH3:19]>O1CCOCC1.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)[C-]1C=CC=C1CN(C)C.[CH-]1C=CC=C1.[Fe+2]>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([CH:18]([CH3:19])[C:17]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[O:20])=[C:3]([CH3:10])[CH:4]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 743431-(4-Pyridinyl)-1-propanoneHCID 41780025-Bromo-2-methoxy-4-methylpyridine

Product 1

HCID 66813038HCID 66813038, compound

Reagents, catalysts & solvents 2

HCID 178483166HCID 178483166, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

5-Bromo-2-methoxy-4-methylpyridine ([CAS Reg. No. 164513-39-7], 202 mg) was added to caesium carbonate (488 mg), 4-propionylpyridine ([CAS Reg. No. 1701-69-5], 165 mg) and chloro(di-2-norbornylphosphino)(2-dimethylaminomethylferrocen-1-yl)palladium (II), ([CAS Reg. No. 614753-51-4], 11 mg) in dioxane (2 ml). The mixture was heated in a sealed tube to 120° C. over night. Purification by preparative HPLC (Phenomenex Gemini Axia-C18 column, solvent gradient 20-95% CH3CN in 0.1% HCOOH[aq]) gave the title compound (30 mg). MS (m/e)=257.1 [M+H+].

Workup

  1. customPurification by preparative HPLC (Phenomenex Gemini Axia-C18 column, solvent gradient 20-95% CH3CN in 0.1% HCOOH[aq])

Sources & evidence

ORD record
ord-0e5f13164dce46b59ff0e7172fb988ad
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

Loading…