N-bromobutanimide → (5E)-5-{(2E)-2-[(1-bromo-2-methylindolizin-3-yl)carbonyl]but-2-en-1-ylidene}-4-methylidene-2-phenyl-4,5-dihydro-6H-1,3-oxazin-6-one

HRID 1502208Notes

Reaction equation

HRID 1502208 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]=[C:10]1[N:11]=[C:12]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:13][C:14](=[O:32])/[C:15]/1=[CH:16]/[C:17](/[C:20]([C:22]1[N:30]2[C:25]([CH:26]=[CH:27][CH:28]=[CH:29]2)=[CH:24][C:23]=1[CH3:31])=[O:21])=[CH:18]\[CH3:19]>C(Cl)Cl.CN1C(=O)CCC1>[Br:1][C:24]1[C:23]([CH3:31])=[C:22]([C:20](/[C:17](=[CH:18]/[CH3:19])/[CH:16]=[C:15]2\[C:10](=[CH2:9])[N:11]=[C:12]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[O:13][C:14]\2=[O:32])=[O:21])[N:30]2[C:25]=1[CH:26]=[CH:27][CH:28]=[CH:29]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 89655795(5E)-4-methylidene-5-{(2E)-2-[(2-methylindolizin-3-yl)carbonyl]but-2-en-1-ylidene}-2-phenyl-4,5-dihydro-6H-1,3-oxazin-6-one

Product 1

HCID 117761369(5E)-5-{(2E)-2-[(1-bromo-2-methylindolizin-3-yl)carbonyl]but-2-en-1-ylidene}-4-methylidene-2-phenyl-4,5-dihydro-6H-1,3-oxazin-6-oneYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-Bromosuccinimide (10.64 g; 59.8 mmol) is added portionwise to a solution of (5E)-4-methylidene-5-{(2E)-2-[(2-methylindolizin-3-yl)carbonyl]but-2-en-1-ylidene}-2-phenyl-4,5-dihydro-6H-1,3-oxazin-6-one (22.8 g; 59.8 mmol) in 350 mL of DCM and 105 mL of NMP. After 10 min of stirring at ambient temperature, the yellow precipitate formed is filtered off, washed with DCM and dried under vacuum to give 23.2 g (85%) of the yellow powder.

Workup

  1. customthe yellow precipitate formed
  2. filtrationis filtered off
  3. washwashed with DCM
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e95183df611b406d81b72606e74c0cdd
Source dataset
uspto-grants-2015_12
Patent number
US09206177B2

Reaction notes

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