N-bromobutanimide → HCID 86681465, compound

HRID 339973Notes

Reaction equation

HRID 339973 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([N:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:32]4[N:36]([CH3:37])[N:35]=[CH:34][CH:33]=4)[CH:29]=3)[C:24]2=[O:38])[CH2:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])[CH:5]=[C:6]([F:8])[CH:7]=1.[Br:39]N1C(=O)CCC1=O>O1CCCC1>[Br:39][C:33]1[CH:34]=[N:35][N:36]([CH3:37])[C:32]=1[C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:38])[N:23]([C@@H:10]([CH2:9][C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=1)[CH2:11][N:12]1[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]1=[O:22])[CH2:31]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86681463HCID 86681463, compound

Product 1

HCID 86681465HCID 86681465, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{(2S)-3-(3,5-difluorophenyl)-2-[5-(1-methyl-1H-pyrazol-5-yl)-1-oxo-1,3-dihydro-2H-isoindol-2-yl]propyl}-1H-isoindole-1,3(2H)-dione (200.0 mg, 0.39 mmol) [prepared in Example 40] in tetrahydrofuran (5 mL) was added N-bromosuccinimide (72.0 mg, 0.404 mmol). The solution was stirred at room temperature for 1 h and then concentrated under reduced pressure. The residue was purified by combi-flash chromatography eluting with EtOAc/hexane (50-100%). The purification afforded 177 mg (77% yield) of the desired product as white solid. LC/MS found: 591.0 (M+1)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by combi-flash chromatography
  3. washeluting with EtOAc/hexane (50-100%)
  4. customThe purification

Sources & evidence

ORD record
ord-42e2dc848744429a808eceac9bd9a8ad
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

Loading…