Sodium Methoxide → 6-chloro-3-methoxy-4-(methoxymethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 588190Notes

Reaction equation

HRID 588190 reaction equation
Br[CH2:2][C:3]1[C:8]2[C:9]([O:31][CH3:32])=[N:10][N:11]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]=2[CH:6]=[C:5]([Cl:33])[N:4]=1.[CH3:34][O-:35].[Na+]>C1COCC1.O>[Cl:33][C:5]1[N:4]=[C:3]([CH2:2][O:35][CH3:34])[C:8]2[C:9]([O:31][CH3:32])=[N:10][N:11]([C:12]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]=2[CH:6]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 1182717894-(bromomethyl)-6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 1182718036-chloro-3-methoxy-4-(methoxymethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(Bromomethyl)-6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (from the synthesis of Intermediate 11B/Step 2; 64 mg, 0.123 mmol) was dissolved in THF (1.5 mL), charged with sodium methoxide (0.080 mL, 0.370 mmol, 4.6 M), and allowed to stir at room temperature for 30 min. The reaction mixture was diluted with water, extracted with ethyl acetate, and washed with brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (5-50% EtOAc/hexanes) to give 6-chloro-3-methoxy-4-(methoxymethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine. MS ESI calc'd. For C28H24ClN3O2 [M+1]+ 470. found 470.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (5-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-135ba99ca1694b1bbfc613acf41ff298
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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