Phenylboronic Acid → HCID 11430655, compound

HRID 1796331Notes

Reaction equation

HRID 1796331 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:12]([NH:18][C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(COC)OC.O>[C:2]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:12]([NH:18][C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 66827Phenylboronic AcidHCID 11236151HCID 11236151, compound

Product 1

HCID 11430655HCID 11430655, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

[3-(4-Bromobenzenesulfonyl)-6-methylpyridin-2-yl]-(2,4,6-trimethylphenyl)-amine, prepared as described in Example 46, (100 mg, 0.225 mmol), phenylboronic acid (32.9 mg, 0.269 mmol), Pd(PPh3)2Cl2 (7.7 mg, 0.011 mmol) and Ba(OH)2.8H2O (84.6 mg, 0.269 mmol) were heated at reflux in 1:1 dimethoxyethane/water (2 mL) for 20 h. The reaction was partitioned between EtOAc (100 mL) and water (20 mL) and the organic extract was washed with brine, dried, and stripped in vacuo. The residue was purified by silica gel chromatography (10% EtOAc/hexanes eluent) to give the title compound as a solid (47 mg, 47% yield), mp 140–141° C. mass spec. (AP+): m/z 443 (M+1).

Workup

  1. temperaturewere heated
  2. customThe reaction was partitioned between EtOAc (100 mL) and water (20 mL)
  3. extractionthe organic extract
  4. washwas washed with brine
  5. customdried
  6. customThe residue was purified by silica gel chromatography (10% EtOAc/hexanes eluent)

Sources & evidence

ORD record
ord-b0bf77381472480ab60df14585dbe7e4
Source dataset
uspto-grants-2006_04
Patent number
US07030145B2

Reaction notes

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