Water → 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 588175Notes

Reaction equation

HRID 588175 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](=[O:30])[NH:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.[C:31]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([O:30][CH3:31])=[N:9][N:10]([C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1182723016-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one2×

Product 1

HCID 1182718976-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one (Intermediate 3B; 194 mg, 0.471 mmol), K2CO3 (132 mg, 0.955 mmol), and iodomethane (0.044 mL, 0.707 mmol) were stirred in DMF (5 mL) at room temperature for 2 h. Water was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was triturated in MeOH to give 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine, which was carried onto the next step without further purification. MS ESI calc'd. For C26H20ClN3O [M+1]+ 426. found 426.

Workup

  1. extractionthe products extracted into EtOAc (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated in MeOH

Sources & evidence

ORD record
ord-2b6b1e1196a84d4ba1a50f9c249d8dea
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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