N-bromobutanimide → 7-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5H-pyrrolo[2,3-b]pyrazine

HRID 1052267Notes

Reaction equation

HRID 1052267 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]3[CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]5)=[CH:24][CH:23]=4)[NH:19][C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Br:35]N1C(=O)CCC1=O>C(Cl)Cl>[Br:35][C:21]1[C:15]2[C:16](=[N:17][CH:18]=[C:13]([CH2:12][CH2:11][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=3)[N:14]=2)[NH:19][C:20]=1[C:22]1[CH:23]=[CH:24][C:25]([N:28]2[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 727924822-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 730571517-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5H-pyrrolo[2,3-b]pyrazineYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5H-pyrrolo[2,3-b]pyrazine (from Example 1, Step 5, 120 mg, 0.262 mmol) in methylene chloride (2 mL), a solution of N-bromosuccinimide (46.7 mg, 0.262 mmol) in methylene chloride (1 mL) was added dropwise at 0° C. After 30 minutes, the reaction was quenched with saturated aqueous NaHCO3, then extracted with methylene chloride. The combined organic layers were dried over MgSO4, and then concentrated. The residue was purified on silica gel (eluting with 0 to 10% MeOH in dichloromethane (DCM)) to give the desired product (110 mg, 78%). LCMS calculated for C27H31BrN5O2 (M+H)+: m/z=536.2. Found: 536.2.

Workup

  1. customthe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel (eluting with 0 to 10% MeOH in dichloromethane (DCM))

Sources & evidence

ORD record
ord-a75d9ad5f61146779ef2a770d9bc90ba
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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