N-Bromosuccinamide → HCID 18175227, compound

HRID 395963Notes

Reaction equation

HRID 395963 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([C:6]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[NH:8]2)=[CH:4][CH:3]=1.[Br:24]NC(=O)CCC(N)=O>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([C:6]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:7]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[NH:8]2)=[CH:4][C:3]=1[Br:24]

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 9926492HCID 9926492, compound

Product 1

HCID 18175227HCID 18175227, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

6-Amino-3-(4-pyridyl)-2-(4-fluorophenyl)-7-aza-indole (17) (250 mg, 0.822 mmol), N-bromosuccinamide (146 mg, 0.822 mmol), and DMF (4 mL) were allowed to stir at 23° C. After 24 h, the reaction was concentrated in vacuo and the residue was purified by flash chromatography (ethyl acetate:hexane 1:1) to afford 6-Amino-5-bromo-3-(4-pyridyl)-2-(4-fluorophenyl)-7-aza-indole (27): Mass Spectrum (CI) 385 (MH+Br81).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customthe residue was purified by flash chromatography (ethyl acetate:hexane 1:1)

Sources & evidence

ORD record
ord-6989e33f510e46e5a60608b30b7fc873
Source dataset
uspto-grants-2003_08
Patent number
US06605634B2

Reaction notes

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