Dimethylformamide → HCID 178483896, compound

HRID 2240089Notes

Reaction equation

HRID 2240089 reaction equation
[C:1]1([S:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([CH:23]=[O:24])[CH:21]=3)[NH:16][N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=[CH:32][CH:33]=1)CBr.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:40][N:41](C=O)[CH3:42]>O>[CH3:40][N:41]([CH3:42])[CH2:32][CH2:33][O:24][CH2:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][N:15]=[C:14]2[S:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 178519381HCID 178519381, compound

Product 1

HCID 178483896HCID 178483896, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(1-naphthylsulfonyl)-1H-indazole-5-carbaldehyde (0.17 g, 0.5 mmoles), 3-chlorobenzyl bromide (0.07 mL, 0.6 mmoles), and cesium carbonate (0.19 g, 0.6 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 normal phase HPLC using as eluent 30% EtOAc/hexane to afford the title compound as an off-white solid (0.18 g, 0.4 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 normal phase HPLC

Sources & evidence

ORD record
ord-752ab8f251c04de98c11e1a8a7671972
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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