Sodium hydride → 2-(Trimethylsilyl)ethyl 4-{4-[(1E)-3-(dimethylamino)-3-oxopropen-1-yl]phenyl}isoquinoline-6-carboxylate

HRID 1959957노트

반응식

HRID 1959957 반응식
C(OP([CH2:9][C:10]([N:12]([CH3:14])[CH3:13])=[O:11])(=O)OCC)C.[H-].[Na+].[CH:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:35]([O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])=[O:36])[CH:33]=3)[CH:28]=[N:27][CH:26]=2)=[CH:21][CH:20]=1)=O.[Cl-].[NH4+]>ClCCl>[CH3:14][N:12]([CH3:13])[C:10](=[O:11])/[CH:9]=[CH:17]/[C:19]1[CH:20]=[CH:21][C:22]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:35]([O:37][CH2:38][CH2:39][Si:40]([CH3:41])([CH3:43])[CH3:42])=[O:36])[CH:33]=3)[CH:28]=[N:27][CH:26]=2)=[CH:23][CH:24]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11127903diethyl N,N-dimethylcarbamoylmethylphosphonateHCID 866619662-(Trimethylsilyl)ethyl 4-(4-formylphenyl)isoquinoline-6-carboxylate

생성물 1

HCID 667305202-(Trimethylsilyl)ethyl 4-{4-[(1E)-3-(dimethylamino)-3-oxopropen-1-yl]phenyl}isoquinoline-6-carboxylate수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diethyl[2-(dimethylamino)-2-oxoethyl]phosphonate (133 mg, 0.597 mmol) was dissolved in dichloromethane (4 mL), to which 55% sodium hydride (21 mg, 0.48 mmol) was added at 0° C., followed by stirring for 10 minutes. To this solution, 2-(trimethylsilyl)ethyl 4-(4-formylphenyl)isoquinoline-6-carboxylate (150 mg, 0.40 mmol) synthesized in Example 13 (13a) was added, followed by stirring for one hour. To the resulting reaction liquid, a saturated aqueous solution of ammonium chloride was added, followed by extraction with ethyl acetate. The resulting organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-35:65, V/V) to give the desired title compound (168 mg, yield 95%).

후처리

  1. additionwas added at 0° C.
  2. stirringby stirring for one hour
  3. customTo the resulting reaction liquid
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resulting organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-35:65, V/V)

출처 및 근거

ORD 기록
ord-7ba8a48ef372433d8085016b481eb4a5
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410273B2

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