Benzodiazepine → N-methylbenzodiazepine

HRID 1768328Notes

Reaction equation

HRID 1768328 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[CH:4][CH:3]=[N:2]1.[CH3:12]I.[H-].[Na+]>[Pd]>[CH3:12][N:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 134664BenzodiazepineHCID 23686416Methyl iodide sodium hydride

Product 1

HCID 12543525N-methylbenzodiazepine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The bromide 20 available from references 9 and 10 was reacted with trimethylsilyacetylene in the presence of a palladium catalyst to provide trimethylsilyl analog 52. This product was methylated with methyl iodide/sodium hydride to give the N-methyl benzodiazepine 54 (XLi 351). This was subjected to fluoride-mediated desilation to furnish 53 (XLi 350) and 55 (XLi 352).

Workup

  1. customto provide trimethylsilyl analog 52

Sources & evidence

ORD record
ord-3975f48cf3444cf6b66bedd6d7a13887
Source dataset
uspto-grants-2007_06
Patent number
US07235656B2

Reaction notes

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