Methanesulfonyl chloride → N-[3-(1-Ethyl-5-fluoro-indan-1-yl)-1-methyl-1H-indol-7-yl]-methanesulfonamide

HRID 13703Notes

Reaction equation

HRID 13703 reaction equation
[CH2:1]([C:3]1([C:13]2[C:21]3[C:16](=[C:17]([NH2:22])[CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:23])[CH:14]=2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1.CCOCC>[CH2:1]([C:3]1([C:13]2[C:21]3[C:16](=[C:17]([NH:22][S:25]([CH3:24])(=[O:27])=[O:26])[CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:23])[CH:14]=2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 115513163-(1-Ethyl-5-fluoro-indan-1-yl)-1-methyl-1H-indol-7-ylamine

Product 1

HCID 11560090N-[3-(1-Ethyl-5-fluoro-indan-1-yl)-1-methyl-1H-indol-7-yl]-methanesulfonamideYield 86%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

Dissolve 3-(1-ethyl-5-fluoro-indan-1-yl)-1-methyl-1H-indol-7-ylamine (0.18 g, 0.58 mmol) in pyridine (3 ml). Add methanesulfonyl chloride (0.05 ml, 0.70 mmol, 1.20 equivalents) and stir at room temperature under nitrogen overnight. Dilute with ether, wash with 1N aqueous hydrochloric acid (2×), dry over anhydrous sodium sulfate, filter, and concentrate solution in vacuo. Purify the residue on silica eluting with 0 to 100% ethyl acetate/hexanes over 25 minutes to provide the title compound as a white solid (0.19 g, 86%). LC-MS m/z 387.1 (M++1).

Workup

  1. washwash with 1N aqueous hydrochloric acid (2×)
  2. dry with materialdry over anhydrous sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate solution in vacuo
  5. customPurify the residue on silica eluting with 0 to 100% ethyl acetate/hexanes over 25 minutes

Sources & evidence

ORD record
ord-a94e3f9f1ed547afa2bf8ec9090a6340
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Reaction notes

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