Ethyl Acetate → HCID 66680416, compound

HRID 1626737Notes

Reaction equation

HRID 1626737 reaction equation
[O:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.Br[C:10]1[CH:11]=[C:12]([CH:29]=[CH:30][CH:31]=1)[O:13][CH2:14][C:15]([NH:17][C:18]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21])=[O:16].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:28][C:25]1[CH:26]=[CH:27][C:18]([NH:17][C:15](=[O:16])[CH2:14][O:13][C:12]2[CH:11]=[CH:10][CH:31]=[C:30]([C:3]3[CH:4]=[CH:5][O:1][CH:2]=3)[CH:29]=2)=[C:19]([CH:24]=1)[C:20]([O:22][CH3:23])=[O:21]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 2734358Furan-3-boronic acidHCID 66680314HCID 66680314, compound

Product 1

HCID 66680416HCID 66680416, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

210 mg (10.7 mmol) of 3-furan boronic acid, 500 mg (7.13 mmol) of methyl 2-{[(3-bromophenoxy)acetyl]amino}-5-chlorobenzoate, 144 mg (0.713 mmol) of tetrakis(triphenylphosphine)palladium(0), and 613 mg (10.7 mmol) of cesium carbonate were heated under reflux for 6 hours in THF (5 mL). After the completion of the reaction, ethyl acetate was added thereto, and the mixture was stirred for 1 hour and filtered using a silica gel pad. After the filtrate was condensed, the obtained crude product was separated and purified by silica gel column chromatography. IPE was added to the resulting solids, followed by collection by filtration, washing with IPE, and drying under reduced pressure at 50° C. for 5 hours, thereby giving 286 mg of methyl 5-chloro-2-({[3-(furan-3-yl)phenoxy]acetyl}amino)benzoate (yield: 59%).

Workup

  1. additionwas added
  2. filtrationfiltered
  3. customcondensed
  4. customthe obtained crude product
  5. customwas separated
  6. custompurified by silica gel column chromatography
  7. additionIPE was added to the resulting solids
  8. filtrationfollowed by collection by filtration
  9. washwashing with IPE
  10. customdrying under reduced pressure at 50° C. for 5 hours

Sources & evidence

ORD record
ord-bc1da41f4b08480b95dc39a9f8f3e850
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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