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Morpholine → Methyl 3-methyl-5-(morpholin-4-yl)-1-benzofuran-2-carboxylate

HRID 2091391
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HRID 2091391 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:14][C:7]1[C:6]2[CH:15]=[C:2]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH:3]=[CH:4][C:5]=2[O:9][C:8]=1[C:10]([O:12][CH3:13])=[O:11]
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참가 물질

7

반응물 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 42967109Methyl 5-bromo-3-methylbenzofuran-2-carboxylate2회

생성물 1

HCID 66778210Methyl 3-methyl-5-(morpholin-4-yl)-1-benzofuran-2-carboxylate수율 13%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 1140Toluene용매

실험 절차

To a solution (100 mL) of methyl 5-bromo-3-methyl-1-benzofuran-2-carboxylate (5.4 g) synthesized in the above-mentioned (1) in toluene were added morpholine (5.2 mL), cesium carbonate (13.0 g), tris(dibenzylideneacetone)dipalladium (0) (0.92 g) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (1.1 g), and the mixture was heated under reflux under argon atmosphere for 20 hr. The reaction mixture was cooled to room temperature, and filtered through celite. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (0.69 g, 13%) as a yellow oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under argon atmosphere for 20 hr
  3. filtrationfiltered through celite
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)

출처 및 근거

ORD 기록
ord-7a68679e4664466f81799a6e84fb82e1
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08436043B2

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