Water → 6-Bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazine

HRID 1052273Notes

Reaction equation

HRID 1052273 reaction equation
[OH-].[K+].O.[Br:4][C:5]1[N:25](S(C2C=CC=CC=2)(=O)=O)[C:8]2=[N:9][CH:10]=[C:11]([CH2:13][CH2:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=3)[N:12]=[C:7]2[CH:6]=1>C1COCC1>[Br:4][C:5]1[NH:25][C:8]2=[N:9][CH:10]=[C:11]([CH2:13][CH2:14][C:15]3[CH:16]=[C:17]([O:23][CH3:24])[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=3)[N:12]=[C:7]2[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 899637236-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 899624376-Bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazineYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

6.0 M Potassium hydroxide in water (0.50 mL, 3.0 mmol) was added to a solution of 6-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (0.5 g, 0.9952 mmol) (from Example 1, Step 4) in THF (10 mL) and then the mixture was stirred at 70° C. for 3 hours. Most of the solvent was removed and the residue was treated with saturated ammonium chloride. The formed precipitate was filtered, washed with water, and dried to provide the desired product (0.34 g, 94%). LCMS calculated for C16H17BrN3O (M+H)+: m/z=362.0. Found 362.0.

Workup

  1. customMost of the solvent was removed
  2. additionthe residue was treated with saturated ammonium chloride
  3. filtrationThe formed precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-917d878a5cd4487bbab8a3591fd1d73c
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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