N-bromobutanimide → HCID 118598699, compound

HRID 1050424Notes

Reaction equation

HRID 1050424 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[C:16]3([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:15]3[C:14](=[O:22])[CH:13]=[CH:12][N:11]([CH3:23])[C:10]=3[C:9]2=[O:24])=[CH:5][CH:4]=1.[Br:27]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.O>[Br:27][C:13]1[C:14](=[O:22])[C:15]2[C:16]3([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:26][CH:25]=3)[C:9](=[O:24])[C:10]=2[N:11]([CH3:23])[CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 118598891HCID 118598891, compound

Product 1

HCID 118598699HCID 118598699, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 6′-(4-methoxybenzyl)-1′-methylspiro[cyclohexane-1,5′-pyrrolo[3,4-b]pyridine]-4′,7′(1′H,6′H)-dione (1.0 mmol, 1 eq) in carbon tetrachloride (25 mL), add N-bromosuccinimide and heat the mixture at 90° C. for 16 h. After completion the mixture was diluted with water and extracted with ethyl acetate. Remove the solvent under reduced pressure to get the crude. Purify the crude by column chromatography to afford 3′-bromo-6′-(4-methoxybenzyl)-1′-methylspiro[cyclohexane-1,5′-pyrrolo[3,4-b]pyridine]-4′,7′(1′H,6′H)-dione (7).

Workup

  1. extractionextracted with ethyl acetate
  2. customRemove the solvent under reduced pressure
  3. customto get the crude
  4. customPurify the crude by column chromatography

Sources & evidence

ORD record
ord-9c2319e723144021a56368157d0e3e30
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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