Benzyl Bromide → HCID 10293520, compound

HRID 1297082Notes

Reaction equation

HRID 1297082 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:21][CH3:22])=[CH:5][C:6]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:11][NH:10][C:9](=[O:19])[CH2:8][C:7]=2[CH:20]=1.[H-].[Na+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH2:25]([N:10]1[C:9](=[O:19])[CH2:8][C:7]2[CH:20]=[C:3]([O:2][CH3:1])[C:4]([O:21][CH3:22])=[CH:5][C:6]=2[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 98609727,8-dimethoxy-1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-one

Product 1

HCID 10293520HCID 10293520, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7,8-dimethoxy-1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-one VIaa (100 mg, 0.34 mmol) in DMF (5 ml), under an inert atmosphere, add NaH in oil (12 mg, 0.30 mmol). Then add dropwise benzyl bromide (40 μl, 0.34 mmol). After 2 hours at room temperature, evaporate the DMF. Take up the residue in CH2Cl2, wash twice with water. Dry the organic phases on Na2SO4. Purify by silica gel column chromatography (AcOEt/hexane, 4:1). Yield: 71%. M: 114–116° C. 1H-NMR (200 MHz, CDCl3): d 3.53–3.64 (m, 2H, CH2), 3.73 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 4.93–5.32 (d, 2H, NCH2Ph), 6.63 (s, 1H, Ar), 6.92 (s, 1H, Ar), 7.20–7.59 (m, 10H, Ar).

Workup

  1. customevaporate the DMF
  2. washwash twice with water
  3. customDry the organic phases on Na2SO4
  4. customPurify by silica gel column chromatography (AcOEt/hexane, 4:1)
  5. custom114–116° C

Sources & evidence

ORD record
ord-f3a0bf8389264638a35d1a526ed84e05
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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