Cesium carbonate → HCID 69656425, compound

HRID 1243617Notes

Reaction equation

HRID 1243617 reaction equation
Cl[C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][N:12]([CH2:20][CH2:21][CH:22]([OH:27])[C:23]([F:26])([F:25])[F:24])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[C:15]([O:14][C:13](=[O:19])[N:12]([CH2:20][CH2:21][CH:22]([O:27][C:2]1[C:3]([C:4]#[N:5])=[CH:6][CH:7]=[C:8]([CH3:10])[N:9]=1)[C:23]([F:26])([F:25])[F:24])[CH3:11])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 5204002-Chloro-6-methylpyridine-3-carbonitrileHCID 21928363tert-butyl N-methyl-N-(4,4,4trifluoro-3-hydroxybutyl)carbamate

Product 1

HCID 69656425HCID 69656425, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-6-methylnicotinonitrile (0.215 g, 1.41 mmol) and tert-butyl N-methyl-N-(4,4,4-trifluoro-3-hydroxybutyl)carbamate (0.345 g, 1.34 mmol) in DMF (6 mL) was treated with caesium carbonate (0.875 g, 2.69 mmol) at ambient temperature. After stirring for 4 days, the mixture was diluted with water and extracted with diethyl ether. The combined organic extracts were washed (water, brine), dried, and evaporated to an orange oil/solid mixture. The crude material was purified by silica gel chromatography, eluting with 100% dichloromethane and 5% methanol/95% dichloromethane (v/v) to give the product as a yellow oil (0.156 g, 31%).

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined organic extracts were washed (water, brine)
  3. customdried
  4. customevaporated to an orange oil/solid mixture
  5. customThe crude material was purified by silica gel chromatography
  6. washeluting with 100% dichloromethane and 5% methanol/95% dichloromethane (v/v)

Sources & evidence

ORD record
ord-8198e276092c4e5ebe52d285a938d94b
Source dataset
uspto-grants-2006_10
Patent number
US07119109B2

Reaction notes

Loading…