Cesium carbonate → HCID 90409690, compound

HRID 2177621Notes

Reaction equation

HRID 2177621 reaction equation
[NH:1]1[C:5]([N:6]2[C:14]3[CH:13]=[CH:12][N:11]=[CH:10][C:9]=3[N:8]=[N:7]2)=[CH:4][CH:3]=[N:2]1.Br[CH2:16][CH2:17][F:18].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:18][CH2:17][CH2:16][N:2]1[CH:3]=[CH:4][C:5]([N:6]2[C:14]3[CH:13]=[CH:12][N:11]=[CH:10][C:9]=3[N:8]=[N:7]2)=[N:1]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 129822-Fluoroethyl bromideHCID 90409160HCID 90409160, compound

Product 1

HCID 90409690HCID 90409690, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Intermediate 48 (50 mg, 0.269 mmol) in DMF (1 mL) was added 1-bromo-2-fluoroethane (41 mg, 0.322 mmol) and Cs2CO3 (263 mg, 0.806 mmol). The reaction was irradiated in a microwave apparatus for 10 min at 120° C. The resulting mixture was filtered, concentrated and purified by chromatography on silica gel eluted with 100% EtOAc to obtain the title compound (62 mg, 88%). MS (ESI) mass calcd. C10H9FN6, 232.1. m/z found, 233.0 [M+H]+.

Workup

  1. customThe reaction was irradiated in a microwave apparatus for 10 min at 120° C
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated
  4. custompurified by chromatography on silica gel
  5. washeluted with 100% EtOAc

Sources & evidence

ORD record
ord-6f0773cc62824e6faa792feada42e2f1
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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