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

HRID 2371267Notes

Reaction equation

HRID 2371267 reaction equation
[C:1]([O:5][C:6](=[O:36])[C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH:15]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[C:16](=[O:25])[NH:17][C:18]2[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=2)[CH3:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C(O)C.C([O-])([O-])=O.[Na+].[Na+].[O:46]1[C:50](B(O)O)=[CH:49][C:48]2[CH:54]=[CH:55][CH:56]=[CH:57][C:47]1=2>COCCOC.O>[C:1]([O:5][C:6](=[O:36])[C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH:15]([C:16](=[O:25])[N:17]([C:47]2[O:46][C:50]3=[CH:49][CH:48]=[CH:54][C:55]3=[CH:56][CH:57]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:26]2[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[CH3:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 674863434-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-methyl-amino}-benzoic Acid Tert-butyl Ester

Product 1

HCID 674866384-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]methyl-amino}-benzoic Acid Tert-butyl EsterYield 125.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

4-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-methyl-amino}-benzoic acid tert-butyl ester (120 mg, 0.19 mmol) was taken up in 8 mL of DME, 4 mL of ethanol and 2 mL of water. Na2CO3 (81 mg, 2.4 mmol), PdCl2(O-tolyl)2, (15 mg, 0.0019 mmol) and benzo[B]furan-2-boronic acid (62 mg, 0.38 mmol) were then added, flushed with nitrogen and heated to reflux for 1 h. Cooled to RT, EtOAc (20 mL) was added, and filtered through a plug of celite. The solvents were removed under reduced pressure to give a yellow viscous solid. Water was added to the solid to give a yellow precipitate, which was filtered and triturated with methanol to give 140 mg of a white solid. LCMS (M+1=589.6)

Workup

  1. customflushed with nitrogen
  2. temperatureheated
  3. temperatureto reflux for 1 h
  4. additionEtOAc (20 mL) was added
  5. filtrationfiltered through a plug of celite
  6. customThe solvents were removed under reduced pressure
  7. customto give a yellow viscous solid
  8. customto give a yellow precipitate, which
  9. filtrationwas filtered
  10. customtriturated with methanol

Sources & evidence

ORD record
ord-7042e3b5aafb44809a6010fe3dffa6cb
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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