Diisopropylamine → HCID 11630726, 화합물

HRID 1878639노트

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HRID 1878639 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 11630726HCID 11630726, 화합물수율 20.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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 TIM (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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cbef53074ec24531a2870e5f8fa61ab2
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314123B2

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