Water → HCID 86729767, compound

HRID 2272610Notes

Reaction equation

HRID 2272610 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:17](=[O:24])[CH2:18][CH:19]([CH3:23])[CH2:20][CH2:21][OH:22])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[Cl:25][C:26]1[CH:33]=[C:32](F)[CH:31]=[CH:30][C:27]=1[C:28]#[N:29].CC(C)([O-])C.[K+].O>C1COCC1>[Cl:25][C:26]1[CH:33]=[C:32]([CH:31]=[CH:30][C:27]=1[C:28]#[N:29])[O:22][CH2:21][CH2:20][CH:19]([CH3:23])[CH2:18][C:17]([NH:16][C:12]1[CH:13]=[CH:14][C:15]2[N:3]([CH2:1][CH3:2])[C:4]3[C:9]([C:10]=2[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 1090002-Chloro-4-fluorobenzonitrileHCID 23665647Potassium tert-butoxideHCID 86729766HCID 86729766, compound

Product 1

HCID 86729767HCID 86729767, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound obtained in Step 2 (500 mg, 1.54 mmol) and 2-chloro-4-fluorobenzonitrile (240 mg, 1.54 mmol) in THF (15 mL) was added potassium t-butoxide (432 mg, 3.85 mmol) at room temperature, and the mixture was stirred for 14 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 75% ethyl acetate/hexane) to give the title compound (458 mg, 0.996 mmol, 64.6%) as a colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 75% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-23b63834058b4922b44f820b256f4ac2
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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