Benzyl Bromide → HCID 59274098, compound

HRID 1364372Notes

Reaction equation

HRID 1364372 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([Br:15])[C:11](=[O:14])[NH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:18]([N:12]1[CH:13]=[C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=[C:10]([Br:15])[C:11]1=[O:14])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 59274099HCID 59274099, compound

Product 1

HCID 59274098HCID 59274098, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-benzyl-3-bromopyridin-2(1H)-one 4 (3.5 g, 13.5 mmol) in dry DMF (100 mL) was added NaH 60% suspension in mineral oil (0.5 g, 16.2 mmol) and stirred for 30 min, followed by the addition of benzyl bromide (0.1.36 g, 7.9 mmol) and mixture further stirred for 1 h at RT. DMF was distilled off and the residue redissolved in EtOAc (250 mL), washed with brine solution (2×100 mL), dried over anhydrous Na2SO4 and EtOAc distilled off to give a yellow syrup, which was purified by column chromatography on silica gel (EtOAc:Hexane, 4:6) to give 5. Yield 3.8 g (83%), yellow solid, mp 89-90° C. 1H NMR (CDCl3, 500 MHz): δ 3.69 (s, 2H, CH2), 5.18 (s, 2H, CH2), 7.11 (d, 1H, CH, J=2 Hz), 7.12-7.39 (m, 10H, Ar—H), 7.60 (d, 1H, CH, J=2 Hz), 13C NMR (CDCl3, 125 MHz): δ 37.4, 53.5, 117.1, 119.1, 126.9, 128.2, 128.2, 128.3, 128.3, 128.6, 128.8, 128.8, 128.9, 128.9, 134.6, 135.8, 138.7, 143.0, 158.3. HRMS (M+H)+ calcd for C19H17BrNO 354.0494, found 354.0455.

Workup

  1. stirringfurther stirred for 1 h at RT
  2. distillationDMF was distilled off
  3. dissolutionthe residue redissolved in EtOAc (250 mL)
  4. washwashed with brine solution (2×100 mL)
  5. dry with materialdried over anhydrous Na2SO4 and EtOAc
  6. distillationdistilled off
  7. customto give a yellow syrup, which
  8. customwas purified by column chromatography on silica gel (EtOAc:Hexane, 4:6)
  9. customto give 5

Sources & evidence

ORD record
ord-3fc7e3bf75b6413f8a1aee863f38aa61
Source dataset
uspto-grants-2011_02
Patent number
US07888375B2

Reaction notes

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