Methanesulfonyl chloride → HCID 86681667, compound

HRID 571252Notes

Reaction equation

HRID 571252 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:6][CH2:5]2.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH3:22][S:23]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:6][CH2:5]2)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86681665HCID 86681665, compound

Product 1

HCID 86681667HCID 86681667, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of benzyl 2-(5-aminoindolin-1-yl)acetate (0.610 g, 2.161 mmol) in pyridine (15 ml), methanesulfonyl chloride (0.251 ml, 3.24 mmol) was added at 0° C. The mixture was allowed to warm to room temperature and stirred for 1 hour. The solvent was removed under vacuum and the residue was partitioned between DCM and water; the organic phase was washed with brine, dried over sodium sulfate and evaporated to dryness. The crude was purified by flash chromatography on silica gel column (petroleum ether:ethyl acetate=70:30 to 60:40) affording benzyl 2-(5-(methylsulfonamido)indolin-1-yl)acetate (0.565 g, 1.568 mmol, 73% yield). MS/ESI+ 361.0 [MH]+.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between DCM and water
  3. washthe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe crude was purified by flash chromatography on silica gel column (petroleum ether:ethyl acetate=70:30 to 60:40)

Sources & evidence

ORD record
ord-d6b851fa081b40aa8ddade51d2476bca
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

Loading…