Ethanol → 4-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]-amino}benzoic Acid

HRID 1755160Notes

Reaction equation

HRID 1755160 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=2)[C:12](=[O:21])[NH:13][C:14]2[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)C.C([O-])([O-])=O.[Na+].[Na+].[O:41]1[C:45](B(O)O)=[CH:44][C:43]2[CH:49]=[CH:50][CH:51]=[CH:52][C:42]1=2>COCCOC.O>[O:41]1[C:42]2=[CH:52][CH:51]=[CH:50][C:49]2=[CH:43][CH:44]=[C:45]1[N:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:12]([CH:11]([NH:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1)[C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)=[O:21]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 674867274-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-amino}-benzoic Acid

Product 1

HCID 674864684-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]-amino}benzoic AcidYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-amino}-benzoic acid acid (340 mg, 0.6 mmol) was taken up in 8 mL of DME, 4 mL of ethanol and 2 mL of water. Na2CO3 (254 mg, 2.4 mmol), PdCl2(O-tolyl)2 (61 mg, 0.0078 mmol) and benzo[B]furan-2-boronic acid (194 mg, 1.2 mmol) were then added, flushed with nitrogen and heated to reflux for 1 h. Cooled to RT, EtOAc (20 mL) was added and extracted with water (20 mL). The organic layer was washed again with water (20 mL), dried over sodium sulfate, filtered and the organic layer was removed under reduced pressure to give a white solid (120 mg, 100%). 1H NMR showed the compound to be very clean and sufficient for the following step.

Workup

  1. customflushed with nitrogen
  2. temperatureheated
  3. temperatureto reflux for 1 h
  4. additionEtOAc (20 mL) was added
  5. extractionextracted with water (20 mL)
  6. washThe organic layer was washed again with water (20 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe organic layer was removed under reduced pressure

Sources & evidence

ORD record
ord-823e890649874919895b696589ea24cb
Source dataset
uspto-grants-2015_10
Patent number
US09169201B2

Reaction notes

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