Methyl iodide → HCID 86603137, compound

HRID 855458Notes

Reaction equation

HRID 855458 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][N:11]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([OH:40])([C:36]([F:39])([F:38])[F:37])[C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)[C:12]([C:14]2[CH:15]=[C:16]([CH3:23])[CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[CH:19]3)=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:41](=O)([O-])[O-].[K+].[K+].CI.[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][N:11]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([O:40][CH3:41])([C:36]([F:39])([F:37])[F:38])[C:32]([F:33])([F:34])[F:35])=[CH:27][CH:26]=2)[C:12]([C:14]2[CH:15]=[C:16]([CH3:23])[CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[CH:19]3)=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 86603138HCID 86603138, compound

Product 1

HCID 86603137HCID 86603137, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 mg of 5-methyl-1H-indole-7-carboxylic acid [2-(3,4-dichloro-phenyl)-ethyl]-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-benzyl]-amide (0.03 mmol) were dissolved in 5 ml DMF and potassium carbonate (9 mg, 0.07 mmol) and methyl iodide (3 μl, 0.05 mmol) were added. The reaction mixture was stirred over night at rt, then saturated ammonium chloride solution was added and the mixture was extracted twice with EtOAc. The combined organic extracts were washed with water and brine, dried with magnesium sulfate, filtrated and concentrated. The remaining residue was purified by silica gel filtration (hexane/EtOAc 1:1). This gave 20 mg (98%) of the title compound as a white foam. MS (ISP) 617.2 (M+H)+.

Workup

  1. extractionthe mixture was extracted twice with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. filtrationThe remaining residue was purified by silica gel filtration (hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-d0c08fca927746f8aca1cd12491d12f3
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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