Water → toluene-4-sulfonic acid 2-[1-(3-chloro-benzyl)-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester

HRID 2240034Notes

Reaction equation

HRID 2240034 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[C:10]1([S:20]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH2:33][CH2:34][O:35][S:36]([C:39]4[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=4)(=[O:38])=[O:37])[CH:30]=3)[NH:25][N:24]=2)(=[O:22])=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:25]1[C:26]2[C:31](=[CH:30][C:29]([O:32][CH2:33][CH2:34][O:35][S:36]([C:39]3[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=3)(=[O:38])=[O:37])=[CH:28][CH:27]=2)[C:23]([S:20]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)(=[O:21])=[O:22])=[N:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 178427773HCID 178427773, compound

Product 1

HCID 58812063toluene-4-sulfonic acid 2-[1-(3-chloro-benzyl)-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl esterYield 63.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Chlorobenzylbromide (0.90 mL, 6.8 mmol) was added to a stirring suspension of toluene-4-sulfonic acid 2-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester (3.24 g, 6.20 mmol) and cesium carbonate (2.21 g, 6.78 mmol) in acetone (80 mL). The mixture was stirred at ambient temperature under nitrogen for 2 hours. It was then poured into excess water and extracted with chloroform. The organic phase was washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography using 30-35% ethyl acetate in hexane. Drying at 65° C. in vacuo for 30 minutes gave toluene-4-sulfonic acid 2-[1-(3-chloro-benzyl)-3-(naphthalene-1-sulfonyl)-1H-indazol -5-yloxy]-ethyl ester as a dark yellow foam (2.55 g, 63.6%); Mass Spectrum (+EI, [M+H]+) m/z 647. 1HNMR (500 MHz, DMSO-d6): δ8.73-8.75 (m, 1H), 8.55-8.57 (m, 1H), 8.27 (d, 1H, J=8.30 Hz), 8.01-8.04 (m, 1H), 7.67-7.75 (m, 4H), 7.56-7.63 (m, 2H), 7.17-7.27 (m, 5H), 7.05-7.07 (m, 2H), 6.98 (dd, 1H, J=9.28 Hz and 2.32 Hz), 5.71 (s, 2H), 4.31-4.33 (m, 2H), 4.15-4.17 (m, 2H), 2.17 ppm (s, 3H). Elemental Analysis for C33H27ClN2O6S2: Calcd: C, 61.25; H, 4.21; N, 4.33; Found: C, 60.93; H, 4.22; N, 4.21.

Workup

  1. extractionextracted with chloroform
  2. washThe organic phase was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. customDrying at 65° C. in vacuo for 30 minutes

Sources & evidence

ORD record
ord-17bfcf4763db4e4ba1f090e9ea796d28
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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