Cesium carbonate → HCID 67231245, compound

HRID 2035663Notes

Reaction equation

HRID 2035663 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([OH:20])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[N+](C1C=CC(S(O[CH2:34][C:35]([C@@H:38]2[CH2:42][O:41][C:40]([CH3:44])([CH3:43])[O:39]2)([CH3:37])[CH3:36])(=O)=O)=CC=1)([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C(=O)C>C(OCC)(=O)C>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][CH2:37][C:35]([C@@H:38]4[CH2:42][O:41][C:40]([CH3:44])([CH3:43])[O:39]4)([CH3:34])[CH3:36])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 86654365HCID 86654365, compoundHCID 136337804HCID 136337804, compound

Product 1

HCID 67231245HCID 67231245, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol (0.25 g, 0.95 mmol), (R)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropyl 4-nitrobenzenesulfonate (0.41 g, 1.1 mmol) and cesium carbonate (0.62 g, 1.9 mmol) were added to minimal amount of N,N-dimethylacetamide and heated to 85° C. The reaction was cooled, ethyl acetate was added and the mixture was sonicated. Solids were filtered off and the filtrate was dried over MgSO4, filtered and evaporated. The crude material was purified on silica gel using isopropyl alcohol containing 2% NH4OH and DCM to yield 30 mg of the desired product (90% pure. The crude material was used without further purification in the next step.

Workup

  1. temperatureThe reaction was cooled
  2. customthe mixture was sonicated
  3. filtrationSolids were filtered off
  4. dry with materialthe filtrate was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was purified on silica gel

Sources & evidence

ORD record
ord-406911b560aa440abb70e05ddd903d92
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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