Methyl iodide → HCID 21310732, compound

HRID 583179Notes

Reaction equation

HRID 583179 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:11]2[C:15]([C:16]([F:19])([F:18])[F:17])=[N:14][N:13]=[N:12]2)[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[H-].[Na+].I[CH3:23]>CN(C=O)C.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([N:11]2[C:15]([C:16]([F:19])([F:17])[F:18])=[N:14][N:13]=[N:12]2)[CH:5]=[C:6]2[C:10]=1[N:9]([CH3:23])[CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21310731HCID 21310731, compound

Product 1

HCID 21310732HCID 21310732, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-bromo-5-(5-trifluoromethyl-tetrazol-1-yl)-1H-indole (115 mg, 0.346 mmol) in DMF (2 mL) was added sodium hydride (80% dispersion in mineral oil) (12 mg, 0.417 mmol). After gas evolution ceased, iodomethane (33 μL, 0.530 mmol) was added, and the mixture was stirred for 2 hours at room temperature. The mixture was diluted with diethyl ether, washed with water, 2N hydrochloric acid, saturated sodium hydrogencarbonate solution, saturated brine solution, dried (MgSO4), and evaporated. Silica gel chromatography eluting with 10% diethyl ether/hexane afforded pure title compound; yield 83 mg of a white solid.

Workup

  1. washwashed with water, 2N hydrochloric acid, saturated sodium hydrogencarbonate solution, saturated brine solution
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. washSilica gel chromatography eluting with 10% diethyl ether/hexane afforded pure title compound

Sources & evidence

ORD record
ord-29466de14e7b40de8d5e14a3251124e1
Source dataset
uspto-grants-1999_07
Patent number
US05929094

Reaction notes

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