Cesium carbonate → HCID 67955438, compound
Reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:15].[Br:16][C:17]1[C:18](Cl)=[N:19][CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O>[Br:16][C:17]1[C:18]([O:15][C:3]2[CH:4]=[CH:5][C:6]3[N:7]([CH2:11][CH:12]4[CH2:14][CH2:13]4)[N:8]=[N:9][C:10]=3[C:2]=2[Cl:1])=[N:19][CH:20]=[CH:21][CH:22]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-ol (8-5, 50 mg, 0.22 mmol, 1 equiv.) was dissolved in dimethylacetamide (1.5 mL) and treated with 3-bromo-2-chloropyridine (50 mg, 0.25 mmol, 1.15 equiv.) and cesium carbonate (146 mg, 0.45 mmol, 2 equiv). The mixture was stirred under microwave irradiation at 140° C. for 1 hour, treated with additional 3-bromo-2-chloropyridine (50 mg, 0.25 mmol, 1.15 equiv.) and cesium carbonate (80 mg, 0.24 mmol, 1 equiv.) and stirred for an additional hour at 140° C. under microwave irradiation. The mixture was extracted from water (50 mL) with ethyl acetate (3×50 mL) and the combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel chromatography (100:0 to 50:50; hexanes:ethyl acetate) to provide the titled compound 395 as a white powder.
Workup
- stirringstirred for an additional hour at 140° C. under microwave irradiation
- extractionThe mixture was extracted from water (50 mL) with ethyl acetate (3×50 mL)
- dry with materialthe combined organic extracts were dried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified via silica gel chromatography (100:0 to 50:50; hexanes:ethyl acetate)
Sources & evidence
- ORD record
- ord-f0c99bc75cbe4140b4fdb94873e11bdf
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975286B2
Reaction notes
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