N-bromobutanimide → HCID 68628857, compound

HRID 1050810Notes

Reaction equation

HRID 1050810 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[C:20]([CH3:23])=[N:21][S:22][C:10]=2[C:9]=1[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:7])[CH2:2][CH2:3][CH3:4].[Br:31]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:5][C:6]([C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[C:20]([CH2:23][Br:31])=[N:21][S:22][C:10]=2[C:9]=1[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 68629838HCID 68629838, compound

Product 1

HCID 68628857HCID 68628857, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 7-(2,2-dimethyl-propionyloxy)-3-methyl-4-phenyl-isothiazolo[4,5-c]pyridine-6-carboxylic acid butyl ester (392 mg) in CCl4 (1.8 mL) was added N-bromosuccinimide (172 mg) and benzoyl peroxide (11.1 mg). The reaction mixture was refluxed for 18 h. After cooling to r.t. the mixture was filtered. The filtrate was concentrated in vacuo and purified by flash chromatography on silica gel. Eluting with 0-20% EtOAc/CH2Cl2 gave the title compound (398 mg) as a yellow oil: MS (m/z) 505.1 (M+1), 507.1 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 18 h
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified by flash chromatography on silica gel
  5. washEluting with 0-20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-c83431dbee6140ffa4cbfb6f6c76f336
Source dataset
uspto-grants-2016_07
Patent number
US09387200B2

Reaction notes

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