N-bromobutanimide → HCID 86701665, compound

HRID 2174043Notes

Reaction equation

HRID 2174043 reaction equation
[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:20])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C1C(=O)N([Br:28])C(=O)C1>CN(C=O)C>[Br:28][C:16]1[CH:17]=[CH:18][C:19]2[N:11]([S:1]([C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=3)(=[O:2])=[O:3])[CH:12]=[CH:13][C:14]=2[C:15]=1[NH2:20]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 10924147HCID 10924147, compound

Product 1

HCID 86701665HCID 86701665, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

To 1-tosyl-1H-indol-4-amine (9.1 g, 31.8 mmol) in DMF (300 mL) at −20° C. was added NBS (5.60 g, 31.5 mmol) and the mixture was stirred at −20° C. After 5 minutes the reaction was quenched with sat. aq. NaHCO3, then with sat. sodium thiosulfate, extracted with EtOAc (three times), dried over MgSO4, filtered and concentrated. The product was purified by flash chromatography (0-100% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 364.9, 366.9 (M+H).

Workup

  1. customAfter 5 minutes the reaction was quenched with sat. aq. NaHCO3
  2. extractionwith sat. sodium thiosulfate, extracted with EtOAc (three times)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography (0-100% EtOAc in heptanes)

Sources & evidence

ORD record
ord-cd1255e4a4fc45e2a37271f6d1ce2f2b
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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