Pyridine → HCID 86681638, compound

HRID 571221Notes

Reaction equation

HRID 571221 reaction equation
Cl.[NH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].N1C=CC=CC=1>C(Cl)Cl>[CH3:18][S:19]([NH:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 86681636HCID 86681636, compound

Product 1

HCID 86681638HCID 86681638, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of ethyl 2-(3-amino-1H-indol-1-yl)acetate hydrochloride (220 mg, 0.864 mmol) in dry DCM (4 ml), cooled at 0° C. under nitrogen, methanesulfonyl chloride (67.3 μl, 0.864 mmol) and dry pyridine (559 μl, 6.91 mmol) were added. After stirring at 0° C. for 4 hours, the mixture was partitioned between 5% aqueous citric acid and DCM; the organic phase was washed with water, dried over Na2SO4 and evaporated to give ethyl 2-(3-(methylsulfonamido)-1H-indol-1-yl)acetate (221 mg, 0.746 mmol, 86% yield). MS/ESI+ 319.0 [MNa]+. This product was used in the next step without any additional purification.

Workup

  1. customthe mixture was partitioned between 5% aqueous citric acid and DCM
  2. washthe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-56b602615acf472cb446fb9d1847bbf8
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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