Benzyl Bromide → HCID 10184069, compound

HRID 1297089Notes

Reaction equation

HRID 1297089 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])[CH:8]([CH2:12][C:6]2[CH:7]=[CH:20][CH:3]=[CH:4][CH:5]=2)[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 10184069HCID 10184069, compoundYield 79%

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 (200 mg, 0.67 mmol) in DMF (10 ml), under an inert atmosphee, add NaH in oil (50 mg, 1.25 mmol). Then add dropwise benzyl bromide (150 μl, 1.26 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: 79%. 1H-NMR (200 MHz, CDCl3): d 3.35–3.56 (m, 2H, CH2Ph), 3.70 (s, 3H, OCH3), 3.80 (m, 1H, CH), 3.97 (s, 3H, OCH3), 4.87 (d, J=10.2, 1H, NCHPh), 5.30 (d, J=10.2, 1H, NCHPh), 6.61 (s, 1H, Ar), 6.93 (s, 1H, Ar), 7.06–7.42 (m, 13H, Ar), 7.59 (d, J=4.8, 2H, Ar). SM: 477 (M+H), 500 (M+H+Na).

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)

Sources & evidence

ORD record
ord-3577637042ed4bf98ac6321f25217bdd
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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