Ethyl Acetate → HCID 86729777, compound

HRID 2272619Notes

Reaction equation

HRID 2272619 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].CC(C)([O-])C.[K+].F[C:32]1[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[C:34]([CH3:40])[CH:33]=1.C(OCC)(=O)C>CN(C=O)C>[C:36]([C:35]1[CH:38]=[CH:39][C:32]([O:22][CH2:21][CH2:20][CH:19]([CH3:23])[CH2:18][C:17]([NH:16][C:12]2[CH:13]=[CH:14][C:15]3[N:3]([CH2:1][CH3:2])[C:4]4[C:9]([C:10]=3[CH:11]=2)=[CH:8][CH:7]=[CH:6][CH:5]=4)=[O:24])=[CH:33][C:34]=1[CH3:40])#[N:37]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 38260554-Fluoro-2-methylbenzonitrileHCID 23665647Potassium tert-butoxideHCID 86729766HCID 86729766, compound

Product 1

HCID 86729777HCID 86729777, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(9-ethyl-9H-carbazol-3-yl)-5-hydroxy-3-methylpentanamide (0.34 g, 1.05 mmol) in DMF (8.0 mL) was added potassium-t-butoxide (0.258 g, 2.31 mmol) under argon atmosphere. The mixture was stirred at room temperature for 15 min, and 4-fluoro-2-methylbenzonitrile (0.212 g, 1.57 mmol) was added thereto. The reaction solution was stirred at room temperature for 14 hr, and ethyl acetate (80 mL) was added thereto. The organic layer was washed with cold water (2×20 mL) and saturated brine (2×20 mL), and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 20 to 30% ethyl acetate/hexane) to give the title compound (0.16 g, 35%) as a white powder.

Workup

  1. stirringThe reaction solution was stirred at room temperature for 14 hr
  2. washThe organic layer was washed with cold water (2×20 mL) and saturated brine (2×20 mL)
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 20 to 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-921012f7a68945649069a3fe1262758c
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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