Triethylsilane → 6-Chloro-3-methoxy-1H-pyrazolo[4,3-c]pyridine

HRID 588183Notes

Reaction equation

HRID 588183 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([O:30][CH3:31])=[N:9][N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:4]=2[CH:3]=1.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([O:30][CH3:31])=[N:9][NH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 1182718976-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 1182718796-Chloro-3-methoxy-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

6-Chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (Example 40, Step 1; 630 mg, 1.479 mmol) was dissolved in TFA (4 mL) and triethylsilane (0.354 mL, 2.219 mmol) was added. The reaction mixture was stirred at room temperature for 1 h. Saturated NaHCO3 was added and the products extracted into EtOAc followed by 3:1 chloroform/IPA. The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was titrated with ether to afford 6-chloro-3-methoxy-1H-pyrazolo[4,3-c]pyridine, which was carried onto the next step without further purification. MS ESI calc'd. For C7H6ClN3O [M+1]+ 184. found 184.

Workup

  1. extractionthe products extracted into EtOAc
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf39ecb859a44d05b33e5a5dad9e4ab2
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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