Diisopropylamine → HCID 66748528, compound

HRID 1749149Notes

Reaction equation

HRID 1749149 reaction equation
[Li]CCCC.C(NC(C)C)(C)C.[CH:13]1([C:17]#[N:18])[CH2:16][CH2:15][CH2:14]1.Br[CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[CH3:21]>C1COCC1>[Cl:28][C:24]1[CH:23]=[C:22]([CH:20]([C:13]2([C:17]#[N:18])[CH2:16][CH2:15][CH2:14]2)[CH3:21])[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 78148CyanocyclobutaneHCID 99208551-(1-Bromoethyl)-3-chlorobenzeneHCID 178418339Butyllithium

Product 1

HCID 66748528HCID 66748528, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (4.7 mL, 11.8 mmol, 2.5 M in hexane) was added to a solution of diisopropylamine (1.13 g, 11.2 mmol) in THF (20 mL) at −78° C. After stirring for 5 min, neat cyclobutanecarbonitrile (0.8 g, 9.87 mmol) was added and the mixture was stirred at −78° C. for 1 hour. Then a solution of Example 44A (2.6 g, 11.8 mmol) in THF (10 mL) was added and the mixture was stirred at −78° C. for 1 h. The mixture was quenched with water and extracted with EtOAc (40 mL). The solvent was evaporated and the residue was used directly in the next step without further purification. LC-MS: m/z 220 (M+H).

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 hour
  2. stirringthe mixture was stirred at −78° C. for 1 h
  3. customThe mixture was quenched with water
  4. extractionextracted with EtOAc (40 mL)
  5. customThe solvent was evaporated
  6. customthe residue was used directly in the next step without further purification

Sources & evidence

ORD record
ord-0473f156d0564ee1b798690296504451
Source dataset
uspto-grants-2015_10
Patent number
US09156788B2

Reaction notes

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