Methanesulfonyl chloride → HCID 86681628, compound

HRID 571215Notes

Reaction equation

HRID 571215 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH2:11][C:12]([O:14][CH3:15])=[O:13].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[CH3:16][S:17]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 64253229HCID 64253229, compound

Product 1

HCID 86681628HCID 86681628, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of crude methyl 2-(4-amino-1H-indol-1-yl)acetate (obtained as reported in Example 15, Step 2, theoretical amount 3.08 mmol) in pyridine (10 ml), methanesulfonyl chloride (464 μl, 5.95 mmol) was added, and the mixture was reacted overnight at room temperature. The solvent was evaporated, and the residue was partitioned between 1N HCl (10 ml) and ethyl acetate (20 ml); the aqueous phase was extracted with ethyl acetate (3×20 ml) and the combined organic layers were dried over sodium sulfate. After evaporation of the solvent, crude methyl 2-(4-(methylsulfonamido)-1H-indol-1-yl)acetate was obtained and used in the next step without any additional purification (620 mg, 2.196 mmol, 71% yield over 3 steps). MS/ESI+ 283.1 [MH]+.

Workup

  1. customthe mixture was reacted overnight at room temperature
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between 1N HCl (10 ml) and ethyl acetate (20 ml)
  4. extractionthe aqueous phase was extracted with ethyl acetate (3×20 ml)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-9080ade2a5eb446c9117e1bef740430a
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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