N-bromobutanimide → HCID 59508087, compound
Reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:18]([NH:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:19])=[CH:13][CH:12]=3)=[CH:7][CH:6]=[CH:5][N:4]=1.[Br:30]N1C(=O)CCC1=O>C1COCC1>[Br:30][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([NH:20][CH2:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[O:19])[CH:15]=2)[NH:10][C:9]=1[C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A suspension of 2-(2-methoxypyridin-3-yl)-N-(3-morpholinopropyl)-1H-indole-5-carboxamide (0.850 g, 0.215 mmol) in 100 ml THF was heated to 60° C. until dissolved. To the solution was added N-bromosuccinimide (0.406 g, 0.263 mmol) and the reaction was allowed to stir for 1.5 hours. The reaction was not complete, so more N-bromosuccinimide (0.062 g, 0.35 mmol; 0.040 g, 0.022 mmol) was added sequentially and the reaction stirred for 10 more minutes after each addition. Upon completion, the reaction was concentrated and to the residue was added 50 ml EtOAC and 100 ml water. The organics were separated, washed with water (50 ml) and brine (25 ml) and concentrated. The crude product was used with no further purification. LCMS: 473 [M+H].
Workup
- dissolutionuntil dissolved
- stirringthe reaction stirred for 10 more minutes
- additionafter each addition
- concentrationUpon completion, the reaction was concentrated and to the residue
- additionwas added 50 ml EtOAC and 100 ml water
- customThe organics were separated
- washwashed with water (50 ml) and brine (25 ml)
- concentrationconcentrated
- customThe crude product was used with no further purification
Sources & evidence
- ORD record
- ord-91889ed1093745c5b71c9786d3576afa
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410144B2
Reaction notes
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