Cesium carbonate → HCID 89590293, compound

HRID 589379Notes

Reaction equation

HRID 589379 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:7][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1)([O-:25])=[O:24]>O1CCCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:7][N:8]2[CH2:30][C:29]2[CH:32]=[CH:33][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 660114-Nitrobenzyl bromideHCID 178470797HCID 178470797, compound

Product 1

HCID 89590293HCID 89590293, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(6-fluoro-1H-indazol-3-yl)acetate (2.08 g, 9.36 mmol) was dissolved in anhydrous tetrahydrofuran (30 mL). Cesium carbonate (9.15 g, 28.1 mmol) was added, and stirred at room temperature for half an hour. Then p-nitro benzyl bromide (2.02 g, 9.35 mmol) was added, and reacted for 16 hours. Then the solid was filtered. The filtrate was concentrated, chromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1) to obtain a yellow solid 1.38 g, at a yield of 41.2%.

Workup

  1. customreacted for 16 hours
  2. filtrationThen the solid was filtered
  3. concentrationThe filtrate was concentrated
  4. customchromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-7fc53cc15faf4228948cd5dd5f9170db
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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