Methyl iodide → HCID 67582419, compound

HRID 343349Notes

Reaction equation

HRID 343349 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH:20](C1C=CN=CC=1)=C.BrC1C=C2C(=CC=1)NC=C2.CI>CN(C)C=O.O>[CH3:20][N:3]1[C:11]2[C:6](=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 75024-VinylpyridineHCID 24758Sodium hydrideHCID 249055-BromoindoleHCID 14204368HCID 14204368, compound

Product 1

HCID 67582419HCID 67582419, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride, 60% dispersion in oil (0.57 g, 14 mmol) was added portionwise to a suspension of (E)-4-(indol-5-yl)ethenylpyridine (2.82 g, 12.8 mmol) [prepared from 4-vinylpyridine and 5-bromoindole by an analogous procedure to Example 16] in dimethylformamide (100 ml). The mixture was stirred at room temperature, under nitrogen, for 1.5 h to give a red solution which was then cooled to 0° C. and treated dropwise with methyl iodide (0.88 ml, 14 mmol). The reaction mixture was stirred at 0° C. under nitrogen for 10 min, allowed to warm to room temperature and stirred for a further 30 min. The resulting suspension was diluted with water (200 ml), the solid collected under suction, washed with 5% aqueous sodium sulfite solution then water and dried in vacuo to afford the title compound as a buff solid (3.07 g); δH (CDCl3) 3.81 (3H, s, N-CH3), 6.51 (1H, dd, J 3.1, 0.7 Hz, 3'-H), 6.98 (1H, d, J 16.3 Hz, CH=CH), 7.07 (1H, d, J 3.1 Hz, 2'-H), 7.31-7.51 (5H, m, CH=CH, ArH), 7.78 (1H, d, J 1.4 Hz, 4'-H), 8.55 (2H, m, 2-H, 6-H-1).

Workup

  1. customto give a red solution which
  2. temperaturewas then cooled to 0° C.
  3. stirringThe reaction mixture was stirred at 0° C. under nitrogen for 10 min
  4. temperatureto warm to room temperature
  5. stirringstirred for a further 30 min
  6. customthe solid collected under suction
  7. washwashed with 5% aqueous sodium sulfite solution
  8. dry with materialwater and dried in vacuo

Sources & evidence

ORD record
ord-753233b30f8b485183eeaa569da1d821
Source dataset
uspto-grants-1999_01
Patent number
US05861407

Reaction notes

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