Cesium fluoride → HCID 59450554, compound

HRID 1948672Notes

Reaction equation

HRID 1948672 reaction equation
F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[Cs+].[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=1B(O)O.[F:32][C:33]1[C:38]([CH2:39][O:40][C:41]2[CH:49]=[CH:48][C:47]3[C@@H:46]4[C@@H:50]([C:51]([O:53][CH2:54][CH3:55])=[O:52])[C@@H:45]4[CH2:44][C:43]=3[CH:42]=2)=[C:37]([CH3:56])[C:36](I)=[CH:35][CH:34]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=1[C:36]1[CH:35]=[CH:34][C:33]([F:32])=[C:38]([CH2:39][O:40][C:41]2[CH:49]=[CH:48][C:47]3[C@@H:46]4[C@@H:50]([C:51]([O:53][CH2:54][CH3:55])=[O:52])[C@@H:45]4[CH2:44][C:43]=3[CH:42]=2)[C:37]=1[CH3:56]

Participants

6

Reactant 4

HCID 25953Cesium fluorideHCID 27343322,6-Dichlorobenzeneboronic acidHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 59450537HCID 59450537, compound

Product 1

HCID 59450554HCID 59450554, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
70 °C

Procedure

To a two-neck round bottom flask with a magnetic stirring bar, was added tris(dibenzylideneacetone)dipalladium(0) (29.5 mg, 0.032 mmol), tri-t-butylphosphonium tetrafluoroborate (18.6 mg, 0.064 mmol), cesium fluoride (652 g, 4.29 mmol), 2,6-dichlorophenylboronic acid (409 mg, 2.15 mmol), and the product of Step E (500 mg, 1.07 mmol). One neck of the flask was connected to a vacuum line while another neck was fitted with an argon balloon. The flask was then purged 8-10 times with argon. The vacuum line was replaced with a septum and anhydrous THF (10 mL) was added by syringe. The mixture was stirred in a 70° C. oil bath for 16 h. The reaction solution was filtrated and concentrated. The residue was carried on to hydrolysis at the next step without purification.

Workup

  1. customOne neck of the flask was connected to a vacuum line while another neck
  2. customwas fitted with an argon balloon
  3. customThe flask was then purged 8-10 times with argon
  4. additionwas added by syringe
  5. filtrationThe reaction solution was filtrated
  6. concentrationconcentrated
  7. customThe residue was carried on to hydrolysis at the next step without purification

Sources & evidence

ORD record
ord-64f55beec47d4a94be6a6f97f9d763b7
Source dataset
uspto-grants-2013_03
Patent number
US08399507B2

Reaction notes

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