Ethyl Acetate → HCID 86729785, compound

HRID 2272630Notes

Reaction equation

HRID 2272630 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][CH2:17][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-:27])C.[K+].F[C:31]1[CH:32]=[C:33]([C:39]#[N:40])[C:34](=[CH:37][CH:38]=1)[C:35]#[N:36].C(OCC)(=O)C>CN(C=O)C>[C:39]([C:33]1[CH:32]=[C:31]([CH:38]=[CH:37][C:34]=1[C:35]#[N:36])[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:27])#[N:40]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 1034231,2-Benzenedicarbonitrile, 4-fluoro-HCID 23665647Potassium tert-butoxideHCID 86729786HCID 86729786, compound

Product 1

HCID 86729785HCID 86729785, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(9-ethyl-9H-carbazol-3-yl)-5-hydroxy-3-methylpentanamine (0.40 g, 1.23 mmol) in DMF (10.0 mL) was added potassium-t-butoxide (0.304 g, 2.71 mmol) under argon atmosphere. The mixture was stirred at room temperature for 15 min, and 4-fluorophthalonitrile (0.270 g, 1.85 mmol) was added thereto. The reaction solution was stirred at room temperature for 14 hr, and ethyl acetate (100 mL) was added thereto. The organic layer was washed with cold water (2×25 mL) and saturated brine (2×25 mL), and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by preparative HPLC to give the title compound (0.285 g, 51%) 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 (2×25 mL) and saturated brine (2×25 mL)
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-daa803672543479ea925a8d029e6326a
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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