Quinoline → HCID 933997, compound

HRID 331042Notes

Reaction equation

HRID 331042 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](C(O)=O)=[C:7]([CH3:12])[N:8]2[CH3:11])=[CH:4][C:3]=1[O:16][CH3:17].N1C2C(=CC=CC=2)C=CC=1>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH3:12])[N:8]2[CH3:11])=[CH:4][C:3]=1[O:16][CH3:17]

Participants

3

Reactant 2

HCID 7047QuinolineHCID 936038HCID 936038, compound

Product 1

HCID 933997HCID 933997, compoundYield 50.1%

Conditions

Temperature
200 °C

Procedure

6-Bromo-5-methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid (1.02 g, 3.42 mmol) was separated into two round bottom flasks (each with 500 mg of material), followed by the addition of quinoline (2 mL) in each flask. The reaction mixture was heated at 200° C. for 4 hours and was cooled to RT. The two reaction mixture was combined and loaded directly on a silica gel column, eluting with a gradient of 0-20% ethyl acetate in cyclohexane, to give title compound (435 mg). LCMS (A): m/z (M+H)+ 254/256, C11H12BrNO requires 253/255 (acidic).

Workup

  1. temperaturewas cooled to RT
  2. customThe two reaction mixture
  3. washeluting with a gradient of 0-20% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-bd131619a43548cb8d8b484213d10d27
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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