Diisopropylamine → HCID 11630726, compound

HRID 1663057Notes

Reaction equation

HRID 1663057 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[CH3:13][N:14]([CH3:27])[C:15]1[CH:16]=[CH:17][C:18]([CH3:26])=[C:19]([CH:25]=1)[C:20]([N:22]([CH3:24])C)=[O:21].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)C#N>C1COCC1>[CH3:27][N:14]([CH3:13])[C:15]1[CH:25]=[C:19]2[C:18]([CH:26]=[C:24]([C:36]3[CH:35]=[CH:32][CH:31]=[C:30]([O:29][CH3:28])[CH:37]=3)[NH:22][C:20]2=[O:21])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 737123-MethoxybenzonitrileHCID 148392265-(Dimethylamino)-N,N,2-trimethylbenzamideHCID 178418339Butyllithium

Product 1

HCID 11630726HCID 11630726, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of diisopropylamine (1.5 g, 15 mmol) in dry THF (10 mL) was added n-BuLi (6 mL of 2.5 M in hexane, 15 mmol) at −78° C. After 30 min, a solution of 5-dimethylamino-2,N,N-trimethylbenzamide (2.06 g, 10 mmol) in THF (15 mL) was added dropwise at −78° C., the red orange solution was stirred at the same temperature for 1 h. The solution of 3-methoxybenzonitrile (1.7 g, 13 mmol) in dry THF (10 mL) were added and the reaction mixture was stirred at −78° C. for 2 h. The reaction solution was quenched with water and extracted with ethyl acetate and dried over sodium sulfate. After removing the solvent, the residue was purified by column chromatography with n-hexane-ethyl acetate (3:1) to afford compound I as yellow solid (596 mg, 20%). 1H NMR (300 MHz, CDCl3) δ: 9.73 (s, 1H), 7.61 (s, 1H), 7.50 (d, J=8.7 Hz, 1H), 7.38 (m, 1H), 7.23-7.22 (m, 3H), 6.96 (m, 1H), 6.74 (s, 1H), 3.90 (s, 3H), 3.09 (s, 6H).

Workup

  1. stirringthe reaction mixture was stirred at −78° C. for 2 h
  2. customThe reaction solution was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customAfter removing the solvent
  6. customthe residue was purified by column chromatography with n-hexane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-5b4c4fc6668c463c9ef4ed59cdfc8d9d
Source dataset
uspto-grants-2011_10
Patent number
US08034829B2

Reaction notes

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