Cesium carbonate → HCID 59632255, compound

HRID 2369071Notes

Reaction equation

HRID 2369071 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:11][C:10]([C:20]([F:23])([F:22])[F:21])=[N:9]1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:31]1[N:36]=[CH:35][CH:34]=[CH:33][N:32]=1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]([O:19][C:31]3[N:36]=[CH:35][CH:34]=[CH:33][N:32]=3)=[CH:17][CH:18]=2)=[CH:11][C:10]([C:20]([F:23])([F:21])[F:22])=[N:9]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 744042-ChloropyrimidineHCID 136081961HCID 136081961, compound

Product 1

HCID 59632255HCID 59632255, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)phenol (ref hydrogenation below) (60 mg, 180 μmol) and Cs2CO3 (140 mg, 400 μmol) in acetonitrile (2 mL) was added 2-chloropyrimidine (66 mg, 580 μmol). The suspension was then heated to 80° C. in an oil bath. After stirring for 16 hours at 80° C. the suspension was filtered through a plug of silica gel (1 g), which was eluted with EtOAc. The filtrate was concentrated under reduced pressure and purified by flash column chromatography eluting with a gradient from 10% to 30% EtOAc/hexane to afford 2-(4-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)phenoxy)pyrimidine (55 mg, 75% yield) as a white powder. MS(ES): 417 [M+H]+.

Workup

  1. filtrationwas filtered through a plug of silica gel (1 g), which
  2. washwas eluted with EtOAc
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. custompurified by flash column chromatography
  5. washeluting with a gradient from 10% to 30% EtOAc/hexane

Sources & evidence

ORD record
ord-f33c1418f0e54384b9c0f0920cb6eab2
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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