2-Mesitylenesulfonyl chloride → 6-(3-methoxy-4-methoxymethoxy-phenyl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole-3-carbaldehyde

HRID 724362Notes

Reaction equation

HRID 724362 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:21]=[C:20]3[C:16]([C:17]([CH:22]=[O:23])=[N:18][NH:19]3)=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][O:11][CH3:12].[C:24]1([CH3:36])[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[C:25]=1[S:32](Cl)(=[O:34])=[O:33].CN(C1C=CC=CN=1)C>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:21]=[C:20]3[C:16]([C:17]([CH:22]=[O:23])=[N:18][N:19]3[S:32]([C:25]3[C:26]([CH3:31])=[CH:27][C:28]([CH3:30])=[CH:29][C:24]=3[CH3:36])(=[O:34])=[O:33])=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][O:11][CH3:12]

Participants

5

Reactant 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 218852-DimethylaminopyridineHCID 178497461HCID 178497461, compound

Product 1

HCID 218776086-(3-methoxy-4-methoxymethoxy-phenyl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole-3-carbaldehydeYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-(3-methoxy-4-methoxymethoxy-phenyl)-1H-indazole-3-carbaldehyde (441 mg, 1.41 mmol, 1.0 equiv) was taken up as a suspension in dichloromethane (15 mL) and was cooled to 0° C. This mixture was treated with mesitylene sulfonyl chloride (324 mg, 1.48 mmol, 1.05 equiv) and dimethylamino pyridine (DMAP) (181 mg, 1.48 mmol, 1.05 equiv). The mixture was allowed to stir for 1 h at 0° C. and was quenched with the addition of water. The mixture was partitioned between water and a 1:1 ethyl acetate/hexane organic layer. The organic material was dried over sodium sulfate, decanted and concentrated under reduced pressure to give crude material which was purified by silica gel chromatography (50 mL silica, 3:7 ethyl acetate/hexane) to give 6-(3-methoxy-4-methoxymethoxy-phenyl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole-3-carbaldehyde (374 mg, 54%): Rf sm 0.17, p 0.53 (ethyl acetate-hexane 4:6); 1H NMR (CDCl3) δ 10.20 (s, 1H), 8.41 (s, 1H), 8.37 (d, 1H, J=8.5 Hz), 7.73 (dd, 1H, J=1.4, 8.4 Hz), 7.3 (m, 3H), 7.08 (s, 2H), 5.36 (s, 2H), 4.08 (s, 3H), 3.71 (s, 3H), 2.74 (s, 6H), 2.40 (s, 3H).

Workup

  1. customwas quenched with the addition of water
  2. customThe mixture was partitioned between water
  3. dry with materialThe organic material was dried over sodium sulfate
  4. customdecanted
  5. concentrationconcentrated under reduced pressure
  6. customto give crude material which
  7. customwas purified by silica gel chromatography (50 mL silica, 3:7 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-14c2679b33c6460f93e3095961de8f33
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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