Hydrochloric Acid → HCID 58437535, compound

HRID 73366Notes

Reaction equation

HRID 73366 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16](N)=[CH:17][CH:18]=3)[C:13]([C:21]#[N:22])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2].[CH3:24][S:25](Cl)(=[O:27])=[O:26].[N:29]1C=CC=CC=1.Cl>ClCCl>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH:29][S:25]([CH3:24])(=[O:27])=[O:26])[CH:18]=3)[C:13]([C:21]#[N:22])=[CH:12]2)=[CH:9][CH:10]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 666172964-(5-Amino-3-cyanoindol-1-yl)benzoic acid ethyl ester

Product 1

HCID 58437535HCID 58437535, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-amino-3-cyanoindol-1-yl)benzoic acid ethyl ester (0.070 g) in dichloromethane (2 mL) were added methanesulfonyl chloride (0.035 g) and pyridine (0.036 g) at room temperature, and this mixture was stirred at room temperature overnight. This reaction mixture was poured into 1 mol/L hydrochloric acid, this resulting mixture was extracted with ethyl acetate. This organic layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90-75/25) to give the title compound (0.046 g).

Workup

  1. extractionthis resulting mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90-75/25)

Sources & evidence

ORD record
ord-92577061ed154d82b5c5d43a37d3807f
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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