(Diethylamino)sulfur trifluoride → HCID 22677439, compound

HRID 1837459Notes

Reaction equation

HRID 1837459 reaction equation
C(N(S(F)(F)[F:7])CC)C.[NH2:10][C:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][CH:18]=2)[N:14]=[C:13]([C:25]([O:27][CH3:28])=[O:26])[C:12]=1[Cl:29]>ClCCl>[NH2:10][C:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][F:7])=[CH:19][CH:18]=2)[N:14]=[C:13]([C:25]([O:27][CH3:28])=[O:26])[C:12]=1[Cl:29]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 22677319HCID 22677319, compound

Product 1

HCID 22677439HCID 22677439, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Diethylamino)sulfur trifluoride (0.73 mL, 5.5 mmol) was added dropwise to a solution of methyl 4-amino-3-chloro-6-(4-hydroxymethylphenyl)pyridine-2-carboxylate (1.46 g, 5.0 mmol) in dichloromethane (35 mL) at 0° C. The reaction mixture was stirred for 15 minutes and then quenched with ice followed by water. The product was extracted with ethyl acetate and the organic phase was washed with brine and concentrated. The residue was purified by column chromatography (dichloromethane/hexane) giving methyl 4-amino-3-chloro-6-(4-fluoromethylphenyl)pyridine-2-carboxylate (480 mg, 1.6 mmol), mp 95-97° C.

Workup

  1. customquenched with ice
  2. extractionThe product was extracted with ethyl acetate
  3. washthe organic phase was washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (dichloromethane/hexane)

Sources & evidence

ORD record
ord-c0dca351a3274eea95bacddc5f3cea64
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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