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Water → HCID 68761050, compound

HRID 79572
Notes
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Reaction equation

HRID 79572 reaction equation
F[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:3]=12.[CH2:14]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN1C(=O)CCC1>[CH2:14]([N:21]1[CH2:26][CH2:25][N:24]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:3]=23)[CH2:23][CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 759941-BenzylpiperazineHCID 687613944-Fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 68761050HCID 68761050, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

4-Fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (0.300 g, 1.66 mmol) and 1-benzylpiperazine (0.350 g, 1.99 mmol) were placed in NMP (3 mL) and heated to 80° C. in a microwave for 30 minutes. The reaction was then poured into water and extracted with MTBE. The organic fractions were dried, filtered, and concentrated. The crude residue was slurried in minimal DCM, and then triturated with hexane to give 4-(4-benzylpiperazin-1-yl)-3-nitro-1H-pyrrolo[2,3-b]pyridine (0.425 g, 76.1% yield).

Workup

  1. extractionextracted with MTBE
  2. customThe organic fractions were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customtriturated with hexane

Sources & evidence

ORD record
ord-95ee44400e434ba191a3e9eec026aa97
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841304B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes