Indomethacin → HCID 67388927, compound

HRID 448168Notes

Reaction equation

HRID 448168 reaction equation
[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23]([OH:25])=[O:24].[Br:26]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[Br:26][CH2:1][C:2]1[N:10]([C:11](=[O:12])[C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C:9]2[C:4]([C:3]=1[CH2:22][C:23]([OH:25])=[O:24])=[CH:5][C:6]([O:20][CH3:21])=[CH:7][CH:8]=2

Participants

4

Reactant 2

HCID 3715IndomethacinHCID 67184N-bromobutanimide

Product 1

HCID 67388927HCID 67388927, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Indomethacin A2 (R3=H, R1a=4-Cl) (1 g, 2.8 mmol) and N-bromosuccinimide (0.539 g, 3.08 mmol) were suspended in tetrachloromethane (50 ml) and kept at room temperature for 12 h. The reaction mixture was heated to boiling and filtered off from succinimide. The solid was washed with hot tetrachloromethane (150 ml). The solvent was evaporated in vacuo. Prepared 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-acetohypobromoanhydride was boiled in CCl4 (50 ml) for 1.5 h. 2-((2-(Bromomethyl)-1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetic acid 1 h (R1=4-chlorobenzoyl, R3═R4═R5═H, R6═CH3) was prepared and used in further reactions without additional purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. filtrationfiltered off from succinimide
  3. washThe solid was washed with hot tetrachloromethane (150 ml)
  4. customThe solvent was evaporated in vacuo
  5. waitPrepared 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-acetohypobromoanhydride was boiled in CCl4 (50 ml) for 1.5 h
  6. customused in further reactions without additional purification

Sources & evidence

ORD record
ord-a3a76a342aa147e59ed7f2fe01ee2f57
Source dataset
uspto-grants-2013_07
Patent number
US08481587B2

Reaction notes

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