Water → HCID 67983998, compound

HRID 330747Notes

Reaction equation

HRID 330747 reaction equation
[O:1]=[S:2]1(=[O:23])[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])=[C:10]([OH:22])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3]1.N1C=CC=CC=1.[C:30](Cl)(=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32].O>C(OC(=O)C)C.C1CCCCC1>[O:23]=[S:2]1(=[O:1])[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:19])[F:20])=[C:10]([O:22][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 57345399HCID 57345399, compound

Product 1

HCID 67983998HCID 67983998, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

To a solution of 6,6-Dioxo-7-(2-trifluoromethyl-phenyl)-5,6-dihydro-thiopyrano[4,3-b]pyridin-8-ol (1.92 g, 5.61 mmol) prepared according to the above Example 1 in methylenehloride (70 ml) was added at 0° C. pyridine (1.77 g, 22.4 mmol), followed by pivaloylchloride (0.744 g, 6.17 mmol). After stirring at room temperature for 16 h methylenehloride and water was added, the organic phase separated and concentrated. Chromatography over silica with ethylacetate/cyclohexane gave 380 mg colourless crystals (0.88 mmol).

Workup

  1. additionwas added
  2. customthe organic phase separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f7d23d7d006f4c8e93c81ce4dbf85e80
Source dataset
uspto-grants-2014_11
Patent number
US08877683B2

Reaction notes

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