Cesium carbonate → HCID 67289090, compound

HRID 511860Notes

Reaction equation

HRID 511860 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:24])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH3:9])=[N:6][CH:7]=1.Br.Br[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:27][O:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:24])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][CH:15]=2)[CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 67292031HCID 67292031, compound

Product 1

HCID 67289090HCID 67289090, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (R)-N-(1-(5-hydroxypyridin-2-yl)ethyl)-2-(4-(trifluoromethyl)phenoxy)acetamide (30 mg, 0.088 mmol), 2-(bromomethyl)pyridine hydrobromide (22 mg, 0.088 mmol), and cesium carbonate (115 mg, 0.35 mmol) in DMF (3 mL) was heated at 90° C. overnight. After cooling, the mixture was filtered through a pad of celite, washed with dichloromethane, the filtrate was concentrated, and the residue was purified by SCX cartridge to give 34 mg (89% yield) of (R)-N-(1-(5-(pyridin-2-ylmethoxy)pyridin-2-yl)ethyl)-2-(4-(trifluoromethyl)phenoxy)a cetamide as a clear colorless oil; LCMS (Method A) m/z: M+1 obs 432, M−1 obs 430

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through a pad of celite
  3. washwashed with dichloromethane
  4. concentrationthe filtrate was concentrated
  5. customthe residue was purified by SCX cartridge

Sources & evidence

ORD record
ord-b88ddc9b256f4c8ebee5df6befbccc8d
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

Loading…