Phenylboronic Acid → HCID 66995204, compound

HRID 1668428Notes

Reaction equation

HRID 1668428 reaction equation
[CH2:1]([O:8][C:9](=[O:39])[N:10]([C@H:12]([C:14](=[O:38])[NH:15][C:16]1[C:17](=[O:37])[N:18]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:25]=2)[C:19](Cl)=[CH:20][CH:21]=1)[CH3:13])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:40]1(B(O)O)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[F-].[K+]>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1COCC1>[CH2:1]([O:8][C:9](=[O:39])[N:10]([C@H:12]([C:14](=[O:38])[NH:15][C:16]1[C:17](=[O:37])[N:18]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:25]=2)[C:19]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:20][CH:21]=1)[CH3:13])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 66995092HCID 66995092, compound

Product 1

HCID 66995204HCID 66995204, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of compound 20C (37 mg, 0.068 mmol), phenyl boronic acid (12 mg, 0.10 mmol) tri-tert-butylphosphonium tetra fluoroborate (16 mg, 0.054 mmol), tris(dibenzylideneacetone) dipalladium (12 mg, 0.027 mmol) and potassium fluoride (61 mg, 1.0 mmol) is added under nitrogen atmosphere anhydrous THF (1.0 mL). The mixture is heated at reflux for 20 hours and is concentrated. The residue is purified by silica gel preparative TLC (40% ethyl acetate in hexane) to provide the title compound 20D (32 mg, 80%):

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 20 hours
  3. concentrationis concentrated
  4. customThe residue is purified by silica gel preparative TLC (40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8864203a05de4e7bae11fe0e54d96cb8
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Reaction notes

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