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

HRID 576252Notes

Reaction equation

HRID 576252 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][OH:19].CS(C)=O.C(N(CC)CC)C.S(O)(O)(=O)=O.N1C=CC=CC=1>ClCCl.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 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 11789763Pyridine sulfateHCID 68943187ethyl 7-bromo-3-(3-hydroxypropyl)-1H-indole-2-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (0° C.) mixture of EXAMPLE 1B (3.26 g) in dichloromethane (5 mL) was added DMSO (1 mL) and triethylamine (0.835 mL) followed by pyridine sulfate (636 mg). The mixture was stirred for 2 hours, diluted with ethyl acetate (150 mL), and washed with 5% HCl, saturated NaHCO3, water and brine and dried (Na2SO4), filtered and concentrated.

Workup

  1. washwashed with 5% HCl, saturated NaHCO3, water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-683fb63454aa48029c3d1b63d5afa456
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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