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Sodium hydride → (R)-8-bromo-6-(5-chloropyridin-2-yl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine

HRID 1485458
Notes
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Reaction equation

HRID 1485458 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[C@H:9]([CH3:16])[CH2:8][NH:7][C:6]=2[CH:17]=1.[H-].[Na+].[Cl:20][C:21]1[CH:22]=[CH:23][C:24](F)=[N:25][CH:26]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[C@H:9]([CH3:16])[CH2:8][N:7]([C:24]3[CH:23]=[CH:22][C:21]([Cl:20])=[CH:26][N:25]=3)[C:6]=2[CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3458175-Chloro-2-fluoropyridineHCID 70978878(R)-8-bromo-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine

Product 1

HCID 70979392(R)-8-bromo-6-(5-chloropyridin-2-yl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepineYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of (R)-8-bromo-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (1.0 g, 3.4 mmol) in DMF (5 mL) was added NaH (280 mg, 6.8 mmol) at 0° C. After 0.5 h, 5-chloro-2-fluoropyridine (540 mg, 4.08 mmol) was added. The mixture was stirred at room temperature overnight. After quenching with H2O (30 mL), the reaction mixture was extracted with ethyl acetate (10 mL*3). The organic layer was washed with brine and dried over sodium sulfate. Concentrated in vacuo gave (R)-8-bromo-6-(5-chloropyridin-2-yl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (1.0 g, crude) for the next step directly. LRMS (M+H+)+: calcd 403.02. found 404.01.

Workup

  1. customAfter quenching with H2O (30 mL)
  2. extractionthe reaction mixture was extracted with ethyl acetate (10 mL*3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentrated in vacuo

Sources & evidence

ORD record
ord-ba3b42f8f54b4b2ea3cdea8619c6f0ef
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09422292B2

Reaction notes

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