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Cesium carbonate → Methyl 5-[(2-methoxyethyl)(methyl)amino]-3-methyl-1-benzofuran-2-carboxylate

HRID 2091396
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HRID 2091396 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.[CH3:16][O:17][CH2:18][CH2:19][NH:20][CH3:21].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]>[CH3:16][O:17][CH2:18][CH2:19][N:20]([CH3:21])[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
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참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 300977(2-Methoxyethyl)(methyl)amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 42967109Methyl 5-bromo-3-methylbenzofuran-2-carboxylate

생성물 1

HCID 66778759Methyl 5-[(2-methoxyethyl)(methyl)amino]-3-methyl-1-benzofuran-2-carboxylate

시약·촉매·용매 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 1140Toluene용매

실험 절차

To a solution (50 mL) of methyl 5-bromo-3-methyl-1-benzofuran-2-carboxylate (2.7 g) synthesized in Example A186(1) in toluene were added 2-methoxy-N-methylethanamine (2.7 g), cesium carbonate (9.8 g), tris(dibenzylideneacetone)dipalladium (0) (0.69 g) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.87 g), and the mixture was heated under reflux under argon atmosphere for 6 hr. The reaction mixture was cooled to room temperature, and filtered through celite, water was added to the filtrate, 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=1:4, volume ratio) to give the title object compound (2.7 g, quantitative) as a yellow oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under argon atmosphere for 6 hr
  3. filtrationfiltered through celite, water
  4. additionwas added to the filtrate
  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=1:4, volume ratio)
  8. customto give the title object compound (2.7 g, quantitative) as a yellow oil

출처 및 근거

ORD 기록
ord-66e70fd064f54cc49d479bbc0ec463e0
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08436043B2

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