Water → HCID 86666460, compound

HRID 872293Notes

Reaction equation

HRID 872293 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([OH:18])=[C:13]([C:14]([F:17])([F:16])[F:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.Cl[C:20]1[C:25]([CH:26]=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C(=O)C>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([O:18][C:20]4[C:25]([CH:26]=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=4)=[C:13]([C:14]([F:16])([F:17])[F:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 7376072-Chloro-3-pyridinecarboxaldehydeHCID 67955453HCID 67955453, compound

Product 1

HCID 86666460HCID 86666460, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1-(Cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-ol (9-5, 35 mg, 0.14 mmol, 1 equiv.) and 2-chloropyridine-3-carbaldehyde (29 mg, 0.20 mmol, 1.5 equiv.) were dissolved in N,N-dimethylacetamide (1.5 mL) and treated with cesium carbonate (89 mg, 0.27 mmol, 2 equiv.). The mixture was irradiated at 100° C. in a microwave reactor for 30 minutes, cooled to ambient temperature and poured into water (30 mL). The mixture was extracted with ethyl acetate (3×20 mL) and the combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo to afford the titled compound 417.

Workup

  1. customThe mixture was irradiated at 100° C. in a microwave reactor for 30 minutes
  2. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  3. dry with materialthe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5025f131d1146938f54cf9a96a997a7
Source dataset
uspto-grants-2015_03
Patent number
US08975286B2

Reaction notes

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