Cesium carbonate → HCID 86610764, compound

HRID 2240069Notes

Reaction equation

HRID 2240069 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][N:12]=[C:11]2[S:15]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)(=[O:17])=[O:16].[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:13]1[C:14]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[O:5][CH2:4][CH2:3][CH2:2][Cl:1])[C:11]([S:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)(=[O:16])=[O:17])=[N:12]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 178527286HCID 178527286, compound

Product 1

HCID 86610764HCID 86610764, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-(3-chloro-propoxy)-3-(naphthalene-1-sulfonyl)-1-H-indazole (0.7 g, 1.75 mmoles), 3-chloro-benzylbromide (0.28 mL, 2.17 mmoles), and cesium carbonate (0.7 g, 2.17 mmoles) in DMF (5 mL) was stirred together in a round bottom flask at room temperature for 10 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 (0.87 g, 1.66 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-6cc0950bbef3497bb110cb79f29990c5
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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