Cesium carbonate → HCID 11197250, compound

HRID 2240906Notes

Reaction equation

HRID 2240906 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][NH:4][C:5]1[CH:6]=[C:7]([C:13]#[N:14])[C:8]([C:11]#[N:12])=[CH:9][CH:10]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26]>CC#N>[C:13]([C:7]1[CH:6]=[C:5]([N:4]([CH2:3][C:2]([F:15])([F:16])[F:1])[CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:10]=[CH:9][C:8]=1[C:11]#[N:12])#[N:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 576337284-[(2,2,2-Trifluoroethyl)amino]-1,2-benzenedicarbonitrile

Product 1

HCID 11197250HCID 11197250, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 4-[(2,2,2-trifluoroethyl)amino]-1,2-benzenedicarbonitrile (0.020 g, 0.089 mmol) in MeCN (3 mL) was treated with Cs2CO3 (0.078 g, 0.24 mmol) and methyl bromoacetate (0.037 g, 0.24 mmol) and heated at 85° C. under nitrogen for 8 h. Upon cooling, the mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (20-100% CH2Cl2-hexanes gradient) and the product crystallized from CH2Cl2-hexanes to give 0.015 g (58% yield) of the title compound as a white solid: MS (ES) m/z 296 (M−1).

Workup

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between EtOAc and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (20-100% CH2Cl2-hexanes gradient)
  7. customthe product crystallized from CH2Cl2-hexanes

Sources & evidence

ORD record
ord-df18a62da7804610ba0b5c91541ba94e
Source dataset
uspto-grants-2010_05
Patent number
US07723385B2

Reaction notes

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