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

HRID 2091396
Notes
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Reaction equation

HRID 2091396 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents

2
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-66e70fd064f54cc49d479bbc0ec463e0
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08436043B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes