Triethylamine → Ethyl 3-(3-(methylsulfonyloxy)propyl)-1h-indole-2-carboxylate

HRID 533234

Reaction equation

HRID 533234 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(#N)C>[CH3:26][S:27]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67316234ethyl 3-(3-hydroxypropyl)-1H-indole-2-carboxylate

Product 1

HCID 87353567Ethyl 3-(3-(methylsulfonyloxy)propyl)-1h-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of EXAMPLE 3A (0.125 g) and triethylamine (0.21 mL) in acetonitrile (3 mL) at 0-5° C. was added methanesulfonyl chloride (0.0404 mL). After 30 minutes, the mixture was concentrated, and the concentrate was purified by flash chromatography on silica gel with 0-30% ethyl acetate/hexanes.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe concentrate was purified by flash chromatography on silica gel with 0-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-22d6a533025f46338385244e57eb3a97
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Linked notes

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