Sodium hydride → HCID 20135077, compound

HRID 580387Notes

Reaction equation

HRID 580387 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH:9]([C:13]([O:15][CH3:16])=[O:14])[CH:8]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH2:7][C:6]=2[CH:25]=1.[H-].[Na+].[CH3:28][O:29][CH2:30]Br>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:28][O:29][CH3:30])[C:10](=[O:12])[CH:9]([C:13]([O:15][CH3:16])=[O:14])[CH:8]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)[CH2:7][C:6]=2[CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 141561947-Chloro-1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one

Product 1

HCID 20135077HCID 20135077, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-chloro-1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (270 mg; 0.75 mmole; see Example 1C) in dimethylformamide (10 ml), cooled at 0°-5° C. in an ice-water bath, was added 50% sodium hydride (72 mg; 1.5 mmole). After stirring at 0°-5° C. for 15 minutes, methoxymethylbromide (240 μ; 3 mmole) was added dropwise. The reaction mixture was allowed to stir at 0°-5° C. for two additional hours. The excess sodium hydride was destroyed by the addition of water, and the resulting mixture was extracted with ether. The aqueous layer was extracted with ether (three times) and the combined organic layers were dried (magnesium sulfate) and concentrated. The crude residue was flash chromatographed (silica gel/5-20% ethyl acetate:hexane) yielding 233 mg of the title compound as an oil.

Workup

  1. stirringto stir at 0°-5° C. for two additional hours
  2. customThe excess sodium hydride was destroyed by the addition of water
  3. extractionthe resulting mixture was extracted with ether
  4. extractionThe aqueous layer was extracted with ether (three times)
  5. dry with materialthe combined organic layers were dried (magnesium sulfate)
  6. concentrationconcentrated
  7. customchromatographed (silica gel/5-20% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-a3390a42a0b342ed87f04e84451c6952
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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