Cesium carbonate → HCID 67315182, compound

HRID 1012603Notes

Reaction equation

HRID 1012603 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[F:9].[CH3:10][O:11][C:12](=[O:30])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=2[Cl:28])[CH:14]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:10][O:11][C:12](=[O:30])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:2]3[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=3[F:9])=[CH:23][C:22]=2[Cl:28])[CH:14]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 676741-Bromo-2,4-difluorobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 67314897HCID 67314897, compound

Product 1

HCID 67315182HCID 67315182, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

1-Bromo-2,4-difluorobenzene (87 μL, 0.77 mmol) was dissolved in 2.5 mL dry toluene under an argon atmosphere. Compound 462 (250 mg, 0.77 mmol) was added and dissolved in the solvent. 4,5-bis-diphenylphosphanyl-9,9-dimethyl-9H-xanthene (13 mg, 0.023 mmol), Pd(OAc)2 (3.5 mg, 0.015 mmol) and Cs2CO3 (352 mg, 1.08 mmol) were added, and the reaction mixture was stirred under an argon atmosphere at 120° C. for 24 h. The reaction mixture was filtered and then purified by flash chromatography using EtOAc/petroleum ether 1:2 as the eluent to afford the title compound as a solid.

Workup

  1. dissolutiondissolved in the solvent
  2. filtrationThe reaction mixture was filtered
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a3b7e94e9abc4fadbf871e92255e8dae
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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