Potassium tert-butoxide → HCID 178487696, compound

HRID 880733Notes

Reaction equation

HRID 880733 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[S:14][CH2:15][CH:16]([C:18]([F:21])([F:20])[F:19])[N:17]=2)=O)=[C:8]([CH3:22])[C:7]([O:23][CH3:24])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CC(C)([O-])C.[K+]>CC(O)(C)C>[CH3:24][O:23][C:7]1[C:8]([CH3:22])=[C:9]2[C:4]([C:1]([OH:3])=[CH:2][C:11]([C:13]3[S:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:17]=3)=[N:10]2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 667303754-trifluoromethyl-4H-thiazole-2-carboxylic acid-(6-acetyl-3-methoxy-2-methyl-phenyl)-amide

Product 1

HCID 178487696HCID 178487696, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of compound 202b (70 g, 1 eq.) in tBuOH (1.2 L) was added potassium t-butoxide (46 g, 2.1 eq.) under nitrogen. The mixture was heated to 70° C. for 16 hrs. The reaction mixture was concentrated under reduced pressure and then acidified to pH 5. The precipitate was filtered, washed with water, and triturated in a diisopropylether/pentane mixture to yield compound 203b as a beige solid in 89% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 2.43 (s, 3H), 3.98 (s, 3H), 6.76 (d, J=1.76 Hz, 1H), 7.04 (d, J=9.10 Hz, 1H), 7.96 (s, 1H), 8.24 (d, J=9.10 Hz, 1H), 9.31 (brs, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customtriturated in a diisopropylether/pentane mixture

Sources & evidence

ORD record
ord-19ec78e3dc5a4289a8b1a61a92b9f239
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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