Methyl iodide → HCID 90409604, compound

HRID 2177605Notes

Reaction equation

HRID 2177605 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][C:14]2[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:18][NH:19][C:13]=2[CH2:12]1)=[O:10].[H-].[Na+].I[CH3:29]>CN(C=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][C:14]2[C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:18][N:19]([CH3:29])[C:13]=2[CH2:12]1)=[O:10].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][C:14]2=[C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:18]([CH3:29])[N:19]=[C:13]2[CH2:12]1)=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 90409322HCID 90409322, compound

Product 1

HCID 90409604HCID 90409604, compoundYield 2,657.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-[(2,3-Dichlorophenyl)carbonyl]-3-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine (35 mg, 0.09 mmol) in DMF (0.5 mL) was added NaH (60%) (5 mg, 0.1 mmol). The reaction was allowed to stir at rt for 1 hr then iodomethane (0.005 mL, 0.09 mmol) was added. The reaction mixture was allowed to stir for 2 hours. After aqueous workup, the resulting mixture was extracted with ethyl acetate. The combined organic layers were dried and concentrated into a yellow residue which was purified via Basic HPLC (0-99% acetonitrile/water (NH4OH)) to afford the desired product 924 mg, 33%). MS (ESI): mass calcd. for C20H17C12N3O, 386.28. m/z found, 387.2 [M+H]+.

Workup

  1. stirringto stir for 2 hours
  2. extractionAfter aqueous workup, the resulting mixture was extracted with ethyl acetate
  3. customThe combined organic layers were dried
  4. concentrationconcentrated into a yellow residue which
  5. customwas purified via Basic HPLC (0-99% acetonitrile/water (NH4OH))

Sources & evidence

ORD record
ord-3d0a73079d354ab087e0dd3c77d4fbdb
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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