N-bromobutanimide → HCID 67248702, compound

HRID 80515Notes

Reaction equation

HRID 80515 reaction equation
[CH2:1]([N:8]1[CH2:23][CH2:22][N:11]2[C:12]3[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=3[NH:14][C:15](=[O:17])[CH2:16][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O>C(O)(=O)C>[CH2:1]([N:8]1[CH2:23][CH2:22][N:11]2[C:12]3[CH:21]=[CH:20][C:19]([Br:24])=[CH:18][C:13]=3[NH:14][C:15](=[O:17])[CH2:16][CH:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58284927HCID 58284927, compound

Product 1

HCID 67248702HCID 67248702, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of Example 112A (1.30 g, 4.23 mmol) in acetic acid (20 mL) was added N-bromosuccinimide (0.828, 4.65 mmol). The reaction stirred for 16 hours. The reaction solution was concentrated, then partitioned between NaOH (1M) and dichloromethane. The dichloromethane layer was separated and concentrated onto silica gel. Purification via flash chromatography (30-100% ethyl acetate/hexanes) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.22-7.38 (m, 6H) 7.07 (d, J=2.37 Hz, 1H), 7.01 (d, J=8.81 Hz, 1H), 3.50-3.58 (m, 2H), 3.24-3.30 (m, 1H), 3.05-3.17 (m, 1H), 2.91-3.01 (m, 1H), 2.71-2.86 (m, 2H), 2.52-2.61 (m, 1H), 2.05-2.25 (m, 2H), 1.90 (d, J=13.22 Hz, 1H); MS (APCI+) m/z 386, 388 (M+H)+.

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompartitioned between NaOH (1M) and dichloromethane
  3. customThe dichloromethane layer was separated
  4. concentrationconcentrated onto silica gel
  5. customPurification via flash chromatography (30-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d7a2bca1fb78485b999b6660e92afe83
Source dataset
uspto-grants-2014_09
Patent number
US08846663B2

Reaction notes

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