Phenol → 2,2-dimethyl-1-[2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one

HRID 600385노트

반응식

HRID 600385 반응식
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1.[C:25]1([OH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1N(C)C)(C)(C)C>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:13][C:12]([CH3:15])([CH3:14])[C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([O:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:3]=2)[N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:9]=1)=[O:16]

참가 물질

7

반응물 4

HCID 996PhenolHCID 62657Potassium Phosphate, TribasicHCID 27349362-Di-tert-butylphosphino-2'-(N,N-dimethylamino)biphenylHCID 578292211-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-yl)-2,2-dimethylpropane-1-one

생성물 1

HCID 578310492,2-dimethyl-1-[2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one수율 62.7%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

A mixture of 1-[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.051 g, 0.12 mmol), phenol (0.017 g, 0.18 mmol), potassium phosphate (0.056 g, 0.26 mmol), 2-di-tert-butylphosphino-2′-(N,N-dimethylamino)biphenyl (0.0041 g, 0.012 mmol) and Pd(OAc)2 (0.002 g, 0.009 mmol) in 1 mL of toluene was stirred at 100° C. for 13 h, then at 150° C. for 4 h. The resulting dark orange mixture was partitioned between 10 mL of ethyl acetate and 10 mL of water. The organic layer was dried over MgSO4, filtered and concentrated to an orange oil. Column chromatography (0-20% EtOAc/hexanes) afforded 0.032 g (62%) of impure 2,2-dimethyl-1-[2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one as a yellow oil, which was used without further purification.

후처리

  1. waitat 150° C. for 4 h
  2. customThe resulting dark orange mixture was partitioned between 10 mL of ethyl acetate and 10 mL of water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an orange oil

출처 및 근거

ORD 기록
ord-efb3b03f13664245898e361fe81a4d0e
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902197B2

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