Water → 2-amino-6-bromo-9H-pyrido[2,3-b]indole-3-carboxamide

HRID 421641Notes

Reaction equation

HRID 421641 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([NH2:17])=[O:16])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:14]=1.[Br:18]N1C(=O)CCC1=O.O>C(#N)C.CN(C)C=O>[NH2:1][C:2]1[C:3]([C:15]([NH2:17])=[O:16])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([Br:18])[CH:12]=3)[NH:7][C:6]=2[N:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 152709842-amino-9H-pyrido[2,3-b]indole-3-carboxamide

Product 1

HCID 249008062-amino-6-bromo-9H-pyrido[2,3-b]indole-3-carboxamideYield 43.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-amino-9H-pyrido[2,3-b]indole-3-carboxamide (5, 35 mg, 0.15 mmol) in acetonitrile (1 mL) and N,N-dimethylformamide (1 mL), was added N-bromosuccinimide (37 mg, 0.209 mmol) in one portion at −10° C. The mixture was warmed to room temperature and stirred for one hour. Water was added and the mixture was extracted with methylene chloride (3×20 mL). Extracts were combined, dried over sodium sulfate, filtered and concetnrated to afford the crude product which was subsequently purified by HPLC (Phenomenex Luna 15 μm C18, aqueous HCOOH/CH3CN) to yield 2-amino-6-bromo-9H-pyrido[2,3-b]indole-3-carboxamide (34, 20 mg, 40%) as yellow solid. NH4OAc standard conditions. DAD Retention Time=6.12 min. M+H=307. 1H NMR (300 MHz, MeOD): δ 8.65 (d, J=6.9 Hz, 1H), 8.03 (d, J=4.9 Hz, 1H), 7.43-7.37 (m, 1H), 7.33-7.27 (m, 1H).

Workup

  1. extractionthe mixture was extracted with methylene chloride (3×20 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customto afford the crude product which
  5. customwas subsequently purified by HPLC (Phenomenex Luna 15 μm C18, aqueous HCOOH/CH3CN)

Sources & evidence

ORD record
ord-444631db385248b1bb4996e69a2b6570
Source dataset
uspto-grants-2012_01
Patent number
US08101604B2

Reaction notes

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