Bromine → HCID 67271637, compound

HRID 250250Notes

Reaction equation

HRID 250250 reaction equation
[Br:1]Br.[CH2:3]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[N:10]([CH:18]2[CH2:20][CH2:19]2)[C:9]=1[CH3:21])=[O:7])[CH3:4]>C(O)(=O)C.O>[CH2:3]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([Br:1])=[C:14]([OH:17])[CH:15]=2)[N:10]([CH:18]2[CH2:19][CH2:20]2)[C:9]=1[CH3:21])=[O:7])[CH3:4]

Participants

5

Reactant 2

HCID 24408BromineHCID 700990HCID 700990, compound

Product 1

HCID 67271637HCID 67271637, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Bromine (277 μL, 5.40 mmol) is added to a suspension of 1-cyclopropyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid ethyl ester (1.40 g, 5.40 mmol) in acetic acid (50 mL). The mixture is stirred for one hour at room temperature. The mixture is diluted with water and the resultant solids are filtered and washed with water. The solids are adsorbed onto silica gel and purified via flash chromatography eluting with 30% THF-heptane. The fractions are combined to yield the title compound (763 mg, 42%). ES/MS m/e 339.8 (M+1).

Workup

  1. filtrationthe resultant solids are filtered
  2. washwashed with water
  3. custompurified via flash chromatography
  4. washeluting with 30% THF-heptane

Sources & evidence

ORD record
ord-a14f9da0062a4c6f9d79392e9104fd7e
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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