N-bromobutanimide → HCID 86681458, compound

HRID 339965Notes

Reaction equation

HRID 339965 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([N:22]2[CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:31]4[N:35]([CH3:36])[N:34]=[CH:33][CH:32]=4)[CH:28]=3)[C:23]2=[O:37])[CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:5]=[CH:6][CH:7]=1.[Br:38]N1C(=O)CCC1=O>O1CCCC1>[Br:38][C:32]1[CH:33]=[N:34][N:35]([CH3:36])[C:31]=1[C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:37])[N:22]([C@@H:9]([CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[CH2:10][N:11]1[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]1=[O:21])[CH2:30]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86681454HCID 86681454, compound

Product 1

HCID 86681458HCID 86681458, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{(2S)-3-(3-fluorophenyl)-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, 0.4044 mmol) [prepared in Example 1] 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 eluted with EtOAc/hexane (50-100%). The purification afforded 231 mg (99.6% yield) of the desired product as white solid. LC/MS found: 573.0 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-7ca5fdaf0ee347e181999cfd8b79bfee
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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