Cesium carbonate → ethyl 2-[1-[[6-(2-naphthamido)pyridin-3-yl]methyl]-1H-indazol-3-yl]acetate

HRID 589393Notes

Reaction equation

HRID 589393 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([NH:30][C:31]([C:33]2[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=2)=[O:32])=[N:28][CH:29]=1>O1CCCC1>[CH:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:41]=[CH:42][C:33]=1[C:31]([NH:30][C:27]1[N:28]=[CH:29][C:24]([CH2:23][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:2]2)=[CH:25][CH:26]=1)=[O:32]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 89590303N-[5-(bromomethyl)pyridin-2-yl]-2-naphthamideHCID 178470794HCID 178470794, compound

Product 1

HCID 89590301ethyl 2-[1-[[6-(2-naphthamido)pyridin-3-yl]methyl]-1H-indazol-3-yl]acetateYield 21.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(1H-indazol-3-yl)acetate (320 mg, 1.57 mmol) was dissolved in anhydrous tetrahydrofuran (50 mL). Cesium carbonate (1.53 g, 4.70 mmol) was added, and stirred at room temperature for half an hour. Then N-[5-(bromomethyl)pyridin-2-yl]-2-naphthamide (532 mg, 1.56 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 light yellow solid 154 mg, at a yield of 21.2%.

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-e1ed6feb01304c2ca8b525c35a7f10f2
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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