Citric Acid → N-ethyl-3-(3-iodo-1H-indazol-6-yl)-4-methylbenzamide

HRID 2246620Notes

Reaction equation

HRID 2246620 reaction equation
[I:1]I.[CH2:3]([NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[N:19][NH:20]3)=[CH:16][CH:15]=2)[CH:8]=1)[CH3:4].S(=O)(O)[O-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1.[OH-].[Na+]>[CH2:3]([NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([I:1])=[N:19][NH:20]3)=[CH:16][CH:15]=2)[CH:8]=1)[CH3:4]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 807IodineHCID 23665763Sodium BisulfiteHCID 60133233HCID 60133233, compound2×

Product 1

HCID 178464761N-ethyl-3-(3-iodo-1H-indazol-6-yl)-4-methylbenzamideYield 96.5%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Iodine (1.35 g) was added to a stirred solution of N-ethyl-3-(1H-indazol-6-yl)-4-methylbenzamide (Intermediate 12, 1.1 g) in 1,4-dioxan (20 ml) and aqueous sodium hydroxide (2M, 20 ml) then stirred at room temperature for 10 min. The reaction mixture was treated with aqueous sodium bisulphite (10%, 25 ml) and aqueous citric acid (10%, 25 ml). The mixture was extracted with ethyl acetate (3×25 ml) and the organic extracts were washed with water (30 ml) dried (Na2SO4) and concentrated under vacuum to give the title-compound (1.54 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×25 ml)
  2. washthe organic extracts were washed with water (30 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1654a3f1b113491397d21ff87ddbf076
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

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