Methyl iodide → HCID 10271777, compound

HRID 1070424Notes

Reaction equation

HRID 1070424 reaction equation
[H-].[Na+].[C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:8]=[CH:7][C:6]([C:9]([N:11]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[N:21][C:15]=3[NH:14][C:13]3[CH:22]=[CH:23][CH:24]=[CH:25][C:12]2=3)=[O:10])=[CH:5][CH:4]=1.[CH3:32]I>CCCCCC.ClCCl>[C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:4]=[CH:5][C:6]([C:9]([N:11]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[N:21][C:15]=3[N:14]([CH3:32])[C:13]3[CH:22]=[CH:23][CH:24]=[CH:25][C:12]2=3)=[O:10])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10270942HCID 10270942, compound

Product 1

HCID 10271777HCID 10271777, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

Sodium hydride (60% suspension, 0.10 g, 2.5 mmol) washed with hexane and dried under nitrogen, was suspended in dry N,N-dimethylformamide (15 mL). Following addition of 1,1′-biphenyl-4-yl-(5,11-dihydro-benzo[b]pyrido[2,3-e][1,4]diazepin-6-yl)-methanone of Example 4 (0.76 g, 2.0 mmol), methyl iodide (0.5 mL, 2.4 mmol) was added. After stirring for 1 hour, the reaction was quenched with water and extracted with dichloromethane The organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give a yellow solid. Purification of the residue by flash chromatography using a solvent gradient from 25% to 35% of ethyl acetate in hexane gave a white foam which was redissolved in dichloromethane, concentrated in vacuo to a foam, then crystallized by sonication from ethyl acetate/hexane to provide the title compound (0.48 g, 61.3%) as a white solid, m.p. 220-223° C.

Workup

  1. customdried under nitrogen
  2. additionwas added
  3. customthe reaction was quenched with water
  4. extractionextracted with dichloromethane The organic layers
  5. dry with materialwere dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a yellow solid
  8. customPurification of the residue by flash chromatography
  9. customgave a white foam which
  10. concentrationconcentrated in vacuo to a foam
  11. customcrystallized by sonication from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c6401082d18d4a50af5863ea4d8b0cc1
Source dataset
uspto-grants-2005_06
Patent number
US06903091B2

Reaction notes

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