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Methyl Acrylate → methyl 6-(dibenzylamino)-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]pyridine-2-carboxylate

HRID 887756
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HRID 887756 반응식
Br[C:2]1[C:3]([C:23]([O:25][CH3:26])=[O:24])=[N:4][C:5]([N:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:52]([O:56][CH3:57])(=[O:55])[CH:53]=[CH2:54]>CN(C)C=O.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:9]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:5]1[N:4]=[C:3]([C:23]([O:25][CH3:26])=[O:24])[C:2](/[CH:54]=[CH:53]/[C:52]([O:56][CH3:57])=[O:55])=[CH:7][CH:6]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
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참가 물질

8

반응물 4

HCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 59145917Methyl 3-bromo-6-(dibenzylamino)pyridine-2-carboxylate

생성물 1

HCID 59145876methyl 6-(dibenzylamino)-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]pyridine-2-carboxylate수율 81.3%

시약·촉매·용매 3

HCID 167845
palladium(II) acetate
촉매
HCID 3283Diethyl Ether용매
HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

A suspension of methyl 3-bromo-6-(dibenzylamino)pyridine-2-carboxylate (3.16 g, 7.68 mmol), palladium acetate (172 mg, 0.768 mmol), triphenylphosphine (404 mg, 1.54 mmol), potassium carbonate-(1.59 g, 11.5 mmol) and methyl acrylate (1.21 mL, 15.4 mmol) in N,N-dimethylformamide (77 mL) was stirred with heating at 120° C. for 12 hr. The reaction solution was diluted with diethyl ether, washed with water and 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 (ethyl acetate/hexane=10/90→40/60) to give the title compound (2.60 g, yield 81%).

후처리

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

출처 및 근거

ORD 기록
ord-aa8b62b95f7f40b28dabe8fd9b9a97e6
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08247429B2

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