Cesium carbonate → 1-(3-Chloro-benzyl)-7-(2-chloro-ethoxy)-5-fluoro-3-(naphthalene-1-sulfonyl)-1H-indazole

HRID 2240059Notes

Reaction equation

HRID 2240059 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([F:27])[CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[C:10]2[S:14]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15].[Cl:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Cl:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32][N:12]1[C:13]2[C:9](=[CH:8][C:7]([F:27])=[CH:6][C:5]=2[O:4][CH2:3][CH2:2][Cl:1])[C:10]([S:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[N:11]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 178527288HCID 178527288, compound

Product 1

HCID 588121191-(3-Chloro-benzyl)-7-(2-chloro-ethoxy)-5-fluoro-3-(naphthalene-1-sulfonyl)-1H-indazoleYield 90.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-(2-chloro-ethoxy)-5-fluoro-3-(naphthalene-1-sulfonyl)-1H-indazole (0.9 g, 2.2 mmoles), 3-chlorobenzyl bromide (0.35 mL, 2.7 mmoles), and cesium carbonate (0.87 g, 2.7 mmoles) in DMF (5 mL) was stirred together in a round bottom flask at room temperature for 30 minutes. Reaction mixture was diluted with H2O, extracted with EtOAc, washed with water (2×), brine (1×), dried over Na2SO4, and concentrated under vacuum. The crude product was purified by HPLC using as eluent 30% EtOAc/hexane to afford the title compound as an off-white solid (0.85 g, 2 mmoles).

Workup

  1. customReaction mixture
  2. extractionextracted with EtOAc
  3. washwashed with water (2×), brine (1×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-ebb03fc083bb40a6aaa79ab0d5d89553
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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