Methyl iodide → HCID 86730667, compound

HRID 332883Notes

Reaction equation

HRID 332883 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:24]=[CH:23][C:15](/[CH:16]=[CH:17]/[C:18]4[N:19]=[N:20][NH:21][N:22]=4)=[CH:14][CH:13]=3)=[C:9]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[S:8][C:7]=2[CH:33]=1.IC.[C:36]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:24]=[CH:23][C:15](/[CH:16]=[CH:17]/[C:18]4[N:22]([CH3:36])[N:21]=[N:20][N:19]=4)=[CH:14][CH:13]=3)=[C:9]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[S:8][C:7]=2[CH:33]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:24]=[CH:23][C:15](/[CH:16]=[CH:17]/[C:18]4[N:22]=[N:21][N:20]([CH3:36])[N:19]=4)=[CH:14][CH:13]=3)=[C:9]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[S:8][C:7]=2[CH:33]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86730669HCID 86730669, compound

Product 2

HCID 86730667HCID 86730667, compoundYield 52%HCID 86730668HCID 86730668, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 30 mL vial containing (E)-5-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)styryl)-2H-tetrazole (15 mg, 0.03 mmol) in DMF (2 mL) was added with iodomethane (2.260 μL, 0.04 mmol) and K2CO3 (13.62 mg, 0.10 mmol) and the reaction was stirred at room temperature for 18 h. The reaction was quenched with sat. aq. NH4Cl (15 mL) and extracted with DCM (25 mL). The organic phase was collected (phase separator) and concentrated in vacuo to afford the crude product. The crude product was purified by reverse phase HPLC (neutral condition, 3% 1-propanol in 1-100% CH3CN/H2O) to afford (E)-5-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)styryl)-1-methyl-1H-tetrazole (8 mg, 0.08 mmol, 52% yield) and (E)-5-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)styryl)-2-methyl-2H-tetrazole (6 mg, 0.01 mmol, 39% yield) both as a white solids.

Workup

  1. customThe reaction was quenched with sat. aq. NH4Cl (15 mL)
  2. extractionextracted with DCM (25 mL)
  3. customThe organic phase was collected (phase separator)
  4. concentrationconcentrated in vacuo
  5. customto afford the crude product
  6. customThe crude product was purified by reverse phase HPLC (neutral condition, 3% 1-propanol in 1-100% CH3CN/H2O)

Sources & evidence

ORD record
ord-4f727486278c4f1ea11df1514189636c
Source dataset
uspto-grants-2014_11
Patent number
US08877801B2

Reaction notes

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