Cesium carbonate → HCID 58542077, compound

HRID 1481297Notes

Reaction equation

HRID 1481297 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][C:12]1[N:16]=[CH:15][NH:14][N:13]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:14]2[CH:15]=[N:16][C:12]([CH3:11])=[N:13]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27735865-Chloro-2-fluorobenzaldehydeHCID 178433329HCID 178433329, compound

Product 1

HCID 58542077HCID 58542077, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

In a 25 ml RBF, a mixture of 5-chloro-2-fluorobenzaldehyde (505 mg, 3.09 mmol), 3-methyl-1H-1,2,4-triazole (270 mg, 3.09 mmol), Cs2CO3 (1007 mg, 3.09 mmol) in DMSO (6179 μl) was heated at 45° C. for 4 hrs and stirred at rt overnight. The reaction mixture was diluted with EtOAc and washed with water. The combined organic phase was washed with brine, dried over MgSO4, filtered, concentrated and purified by flash chromatography to yield 74A as white solid product (140 mg, 20%). 1H NMR (400 MHz, DMSO-d6) δ ppm: 9.95 (s, 1H), 9.02 (s, 1H), 7.96-7.88 (m, 2H), 7.80 (d, J=8.4 Hz, 1H), 2.37 (s, 3H).

Workup

  1. washwashed with water
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-6c34c36c24bd4ad5ace972c4873c723d
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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