Indole → HCID 71253210, compound

HRID 1028985Notes

Reaction equation

HRID 1028985 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1)=[O:6]

Participants

6

Reactant 3

HCID 798IndoleHCID 10868DicyclohexylcarbodiimideHCID 27355882-Bromo-3-methylbenzoic acid

Product 1

HCID 71253210HCID 71253210, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-3-methylbenzoic acid (1.0 g, 4.65 mmol) and 1H-indole (0.60 g, 5.12 mmol) in DCM (23.3 mL) at RT was added DCC (1.15 g, 5.58 mmol) and 4-dimethylaminopyridine (0.11 g, 0.93 mmol). The reaction was stirred at RT overnight. The reaction was quenched with water and the aqueous layer was extracted with EtOAc. The organic layer was then washed with water and brine (3× ea.), dried over Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography (0-50% Hexene/EtOAC) to yield (2-bromo-3-methylphenyl)(1H-indol-1-yl)methanone as a clear oil.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe organic layer was then washed with water and brine (3× ea.)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by column chromatography (0-50% Hexene/EtOAC)

Sources & evidence

ORD record
ord-11b4e26672f74acbb75e8550aadc256d
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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