Triethylamine → ethyl 7-bromo-3-(3-oxopropyl)-1H-indole-2-carboxylate

HRID 576279Notes

Reaction equation

HRID 576279 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][O:19]C1C2C(=CC=CC=2)C=CC=1.C(N(CC)CC)C.N1C=CC=CC=1S([O-])(=O)=O>ClCCl.CS(C)=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH:18]=[O:19]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 4658711Pyridine-2-sulfonateHCID 68938945ethyl 7-bromo-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

Product 1

HCID 86628021ethyl 7-bromo-3-(3-oxopropyl)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 7-bromo-3-(4-hydroxypropyl)-1H-indole-2-carboxylate (EXAMPLE 1C) (3.4 g) and triethylamine (8.5 ml) in dichloromethane (100 ml) and dimethylsulfoxide (10 mL), cooled to 0° C., was added pyridine-2-sulfonate (9.54 g). The mixture was stirred for 3 hours and diluted with ethyl acetate (300 ml) and washed with 5% HCl, water, and brine. After drying the combined organic layers over Na2SO4, the filtrate was concentrated and the crude product was purified by flash chromatography on a silica gel, eluting with 10% ethyl acetate in hexane.

Workup

  1. washwashed with 5% HCl, water, and brine
  2. dry with materialAfter drying the combined organic layers over Na2SO4
  3. concentrationthe filtrate was concentrated
  4. customthe crude product was purified by flash chromatography on a silica gel
  5. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3ef59e6fd23c43abbf9173e832e1c41b
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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