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Sodium Bicarbonate → 2-bromo-3-chloro-5H-pyrrolo[2,3-b]pyrazine

HRID 523024
Notes
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Reaction equation

HRID 523024 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:10]#[C:11][Si](C)(C)C)[C:5]([NH2:9])=[N:6][C:7]=1[Cl:8].CC([O-])(C)C.[K+].C([O-])(O)=O.[Na+]>C1COCC1.O>[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[CH:11][NH:9][C:5]2=[N:6][C:7]=1[Cl:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 900409205-Bromo-6-chloro-3-trimethylsilanylethynyl-pyrazin-2-ylamine

Product 1

HCID 900413612-bromo-3-chloro-5H-pyrrolo[2,3-b]pyrazineYield 107.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-bromo-6-chloro-3-trimethylsilanylethynyl-pyrazin-2-ylamine (2.0 g, 6.58 mmol) in THF (28 mL) was added a 1 M solution of KOtBu in THF (7.24 mL, 7.24 mmol) slowly at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 10 min and then warmed to room temperature. After 2 h, the mixture was concentrated in vacuo and the residue obtained was suspended in water (7.5 mL) and saturated aqueous NaHCO3 (7.5 mL) and stirred overnight at room temperature The solid was filtered, washed with water and hexanes then dried in an oven at 80° C. to give 2-bromo-3-chloro-5H-pyrrolo[2,3-b]pyrazine (1.64 g) as brown solid. LC-MS: 232 (M−H). This was used directly without further purification.

Workup

  1. temperaturewarmed to room temperature
  2. waitAfter 2 h
  3. concentrationthe mixture was concentrated in vacuo
  4. customthe residue obtained
  5. filtrationwas filtered
  6. washwashed with water and hexanes
  7. customthen dried in an oven at 80° C.

Sources & evidence

ORD record
ord-e8f33d4dadd64556a80205e3d01effdf
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09334278B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes