Potassium tert-butoxide → HCID 66992133, compound

HRID 557423Notes

Reaction equation

HRID 557423 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:12]=[C:13]([C:19](=O)[CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=1)[O:8][C:7]([CH3:22])=[CH:6][C:5]2=[O:23].[NH2:24][C:25]([C:29]([F:32])([F:31])[F:30])=[CH:26][C:27]#[N:28].CC(C)([O-])C.[K+]>CC(O)C>[C:27]([C:26]1[CH:12]([C:10]2[CH:11]=[C:2]([F:1])[CH:3]=[C:4]3[C:9]=2[O:8][C:7]([CH3:22])=[CH:6][C:5]3=[O:23])[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:19]([CH3:20])[NH:24][C:25]=1[C:29]([F:32])([F:31])[F:30])#[N:28]

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 534010963-Amino-4,4,4-trifluorobut-2-enenitrileHCID 66991191Ethyl 2-[(6-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate

Product 1

HCID 66992133HCID 66992133, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 230 mg (0.72 mmol) of ethyl 2-[(6-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-methylene]-3-oxobutanoate in 10 ml of 2-propanol is mixed with 98.34 mg (0.72 mmol) of 3-amino-4,4,4-trifluorobut-2-enenitrile [preparation in analogy to K. Krespan, J. Org. Chem. 34, 42-45 (1969)] and 12.2 mg (0.11 mmol) of potassium tert-butoxide and stirred under reflux for 12 h. After cooling, the mixture is concentrated. The residue is purified on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1). The resulting crystals are purified further by preparative HPLC. 27.4 mg (8.69% of theory) of the title compound are obtained as yellow crystals.

Workup

  1. temperatureunder reflux for 12 h
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. customThe residue is purified on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1)
  5. customThe resulting crystals are purified further by preparative HPLC

Sources & evidence

ORD record
ord-a71fc54e44574bf88c1f1eeeda217546
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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