N-bromobutanimide → HCID 67248702, compound

HRID 1896132Notes

Reaction equation

HRID 1896132 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 (1 M) 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, 6 H), 7.07 (d, J=2.37 Hz, 1 H), 7.01 (d, J=8.81 Hz, 1 H), 3.50-3.58 (m, 2 H), 3.24-3.30 (m, 1 H), 3.05-3.17 (m, 1 H), 2.91-3.01 (m, 1 H), 2.71-2.86 (m, 2 H), 2.52-2.61 (m, 1 H), 2.05-2.25 (m, 2 H), 1.90 (d, J=13.22 Hz, 1 H); MS (APCI+) m/z 386, 388 (M+H)+.

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompartitioned between NaOH (1 M) 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-3c4ce360bb044778bdd62594e756e45b
Source dataset
uspto-grants-2013_08
Patent number
US08518933B2

Reaction notes

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