Methyl iodide → HCID 70341501, compound

HRID 1198558Notes

Reaction equation

HRID 1198558 reaction equation
[C:1]([CH2:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16](/[CH:20]=[CH:21]/[C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][C:26]([Cl:32])=[CH:27][CH:28]=4)[N:23]=3)[CH:15]=2)=[CH:6][CH:5]=1)#[N:2].[CH3:33]I.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl.O>[C:1]([CH:3]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16](/[CH:20]=[CH:21]/[C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][C:26]([Cl:32])=[CH:27][CH:28]=4)[N:23]=3)[CH:15]=2)=[CH:6][CH:5]=1)[CH3:33])#[N:2]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 19102584HCID 19102584, compound

Product 1

HCID 70341501HCID 70341501, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-(cyanomethyl)-1-[3-{2(E)-(7-chloroquinolin-2-yl)ethenyl}benzyl]indole (Example 29b) (180 mg, 0.41 mmol), methyl iodide (77 μl, 1.24 mmol) and benzyl-triethyl-ammonium chloride (94 mg, 0.41 mmol) in dichloromethane (3 ml) was stirred with a solution of sodium hydroxide (1.5 g) in water (1.5 ml) heating under reflux for 2 hours. The mixture was diluted with dichloromethane and water and the aqueous layer was extracted with further dichloromethane. The combined solvent layer was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:3). The resulting crude product was further purified by RP-HPLC on a C18 column (eluting with 85 methanol:15 water:0.1 acetic acid) followed by crystallisation from methanol-water.

Workup

  1. temperatureheating
  2. temperatureunder reflux for 2 hours
  3. extractionthe aqueous layer was extracted with further dichloromethane
  4. customThe combined solvent layer was dried
  5. customevaporated
  6. customthe residue was chromatographed on silica in ethyl acetate-hexane (1:3)
  7. customThe resulting crude product was further purified by RP-HPLC on a C18 column (eluting with 85 methanol:15 water:0.1 acetic acid)
  8. customfollowed by crystallisation from methanol-water

Sources & evidence

ORD record
ord-a26ad6ff849c42059594e1bf3730f06f
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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