N-bromobutanimide → HCID 178451611, compound

HRID 2383429Notes

Reaction equation

HRID 2383429 reaction equation
[CH:1]1[C:13]2[C:12]3[CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][C:7]=3[CH:6]=[N:5][C:4]=2[NH:3][N:2]=1.[Br:21]N1C(=O)CCC1=O>ClCCl>[Br:21][C:1]1[C:13]2[C:12]3[CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][C:7]=3[CH:6]=[N:5][C:4]=2[NH:3][N:2]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 46836774tert-butyl 8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate

Product 1

HCID 178451611HCID 178451611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate (0.301 g, 1.09 mmol) in dichloromethane (10 mL) was added N-bromosuccinimide (0.293 g, 1.64 mmol). The reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched by adding aqueous Na2CO3. The organic layer was separated, washed with brine (10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to give a residue. The crude product was purified by flash column chromatography (SiO2, 30% EtOAc in hexanes) to give the desired product. tert-butyl 1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate (0.258 g, 67%) as a foamy white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.94 (s, 1H), 8.40 (s, 1H), 4.63 (s, 2H), 3.67 (m, 2H), 3.28 (m, 2H), 1.44 (s, 9H); LCMS [M+H]: 353.

Workup

  1. customThe reaction was quenched
  2. additionby adding aqueous Na2CO3
  3. customThe organic layer was separated
  4. washwashed with brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue
  9. customThe crude product was purified by flash column chromatography (SiO2, 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c2f7f5c3616e44f2ac96c44e7e1753b4
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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