Tin tetrachloride → HCID 66850944, compound

HRID 1466621Notes

Reaction equation

HRID 1466621 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:14](COCC[Si](C)(C)C)[N:13]=[CH:12][C:11]=2[NH:23]C(=O)OC(C)(C)C)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[Sn](Cl)(Cl)(Cl)Cl>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:14][N:13]=[CH:12][C:11]=2[NH2:23])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 66850735HCID 66850735, compound

Product 1

HCID 66850944HCID 66850944, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 5-(5-chloro-2-methoxypyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-ylcarbamate (211.7 mg, 0.4652 mmol) in 5 mL ethyl acetate was added tin tetrachloride (0.52 mL, 4.4 mmol). The reaction mixture was stirred at room temperature for 2 hours and then evaporated in vacuo. The residual oil was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, and the aqueous layer extracted twice more with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (0 to 20% methanol in dichloromethane) to yield 32.4 mg (31%) of 5-(5-chloro-2-methoxypyridin-3-yl)-1H-pyrazol-4-amine LCMS (ESI) m+H=225.1.

Workup

  1. customevaporated in vacuo
  2. customThe residual oil was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. extractionthe aqueous layer extracted twice more with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude product was purified via flash chromatography on silica gel (0 to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-48db7e3e2cdc40eebbe574235730a012
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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