Cesium carbonate → HCID 89590306, compound

HRID 589374Notes

Reaction equation

HRID 589374 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].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:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:30][C:29]1[CH:32]=[CH:33][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=1)[N:6]=[C:5]2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 660114-Nitrobenzyl bromideHCID 178470795HCID 178470795, compound

Product 1

HCID 89590306HCID 89590306, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(5-fluoro-1H-indazol-3-yl)acetate (0.48 g, 2.16 mmol) was dissolved in anhydrous tetrahydrofuran (30 mL). Cesium carbonate (2.11 g, 6.48 mmol) was added, and stirred at room temperature for half an hour. Then p-nitro benzyl bromide (466 mg, 2.16 mmol) was added. After reacted for 16 hours, 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 295 mg, at a yield of 38.2%.

Workup

  1. customAfter reacted for 16 hours
  2. filtrationthe 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-417492ccfdd944a9b107c02a4b3f9a36
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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