N-bromobutanimide → HCID 118021825, compound

HRID 518566Notes

Reaction equation

HRID 518566 reaction equation
[CH2:1]([CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=2)[O:4]1)[CH3:2].C1C(=O)N([Br:25])C(=O)C1>C(#N)C>[Br:25][C:6]1[CH:7]=[C:8]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=[C:10]2[C:5]=1[O:4][CH:3]([CH2:1][CH3:2])[CH2:12][CH2:11]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118021858HCID 118021858, compound

Product 1

HCID 118021825HCID 118021825, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the title compound from Step 5 (170 mg, 0.667 mmol) in ACN (6 mL) was added NBS (156 mg, 0.867 mmol). The mixture was stirred for 7 h at rt. It was then extracted with DCM, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified with prep-TLC (PE/EA 3:1) to give the title compound (105 mg, 47%) as a gray solid. 1H NMR (400 MHz, CDCl3): δ 7.23 (d, J=2.4 Hz, 1H), 6.96 (d, J=2.4 Hz, 1H), 6.24 (s, 1H), 4.01-3.99 (m, 1H), 2.97 (s, 3H), 2.84-2.77 (m, 2H), 2.04-1.99 (m, 1H), 1.85-1.66 (m, 3H), 1.09 (t, J=7.2 Hz, 3H).

Workup

  1. extractionIt was then extracted with DCM
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with prep-TLC (PE/EA 3:1)

Sources & evidence

ORD record
ord-cebc4c7bc39047ebb90db23e2dd78d72
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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