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Sodium Bicarbonate → N-(5-{2-[4-(5-formyl-2-thienyl)phenyl]ethyl}-2,2-dimethyl-1,3-dioxan-5-yl)acetamide

HRID 1641570
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HRID 1641570 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([NH:18][C:19](=[O:21])[CH3:20])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]2)=[CH:4][CH:3]=1.[CH:22]([C:24]1[S:28][C:27](B(O)O)=[CH:26][CH:25]=1)=[O:23].C(=O)([O-])O.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:22]([C:24]1[S:28][C:27]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]3([NH:18][C:19](=[O:21])[CH3:20])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]3)=[CH:4][CH:3]=2)=[CH:26][CH:25]=1)=[O:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 516892Sodium BicarbonateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 27734305-Formyl-2-thiopheneboronic acidHCID 46202882N-{5-[2-(4-bromophenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide

생성물 1

HCID 57624621N-(5-{2-[4-(5-formyl-2-thienyl)phenyl]ethyl}-2,2-dimethyl-1,3-dioxan-5-yl)acetamide수율 21.5%

시약·촉매·용매

3
HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixed solution of N-{5-[2-(4-bromophenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide (1.07 g) of Reference Example 5, 5-formyl-2-thiopheneboronic acid (0.56 g), sodium hydrogen carbonate (1.51 g), palladium(II) acetate (33.7 mg) and 2-(di-t-butylphosphino)biphenyl (89.5 mg) in 1,2-dimethoxyethane (12 mL)-water (4 mL) was stirred at 65° C. for 9 hr under a nitrogen atmosphere. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (0.25 g) as brown crystals.

후처리

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-2a17d82e6e78402c8ea7b64e743f3c12
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08114902B2

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