Cesium carbonate → [2-Chloro-4-(2-nitro-phenylamino)-phenyl]-{2-methyl-4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-methanone

HRID 1012606Notes

Reaction equation

HRID 1012606 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][O:31]3)=[CH:22][C:21]=2[CH3:36])=[O:19])=[C:14]([Cl:37])[CH:13]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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].O.CCOC(C)=O>[Cl:37][C:14]1[CH:13]=[C:12]([NH:11][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:17]=[CH:16][C:15]=1[C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)=[CH:22][C:21]=1[CH3:36])=[O:19]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 69115o-IodonitrobenzeneHCID 634876Binap, (A+-)-HCID 67313818(4-Amino-2-chloro-phenyl)-{2-methyl-4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-methanone

Product 1

HCID 58677600[2-Chloro-4-(2-nitro-phenylamino)-phenyl]-{2-methyl-4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-methanone

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1-Iodo-2-nitro-benzene (1.38 g, 5.54 mmol) was dissolved in 40 mL dry 1,4-dioxane under an argon atmosphere. Compound 471 (1.77 g, 4.54 mmol) was added and dissolved in the solvent. Rac-BINAP (106 mg, 0.17 mmol), Pd2(dba)3 (104 mg, 0.11 mmol) and Cs2CO3 (2.07 g, 6.30 mmol) were added, and the reaction mixture was stirred under an argon atmosphere at 100° C. for 24 h. The reaction mixture was poured into a mixture of EtOAc and water. The aqueous phase was washed with more EtOAc. The organic phases were combined and washed with brine, dried (MgSO4), filtered and then purified by flash chromatography using EtOAc/petroleum ether 1:5 as the eluent to afford the title compound.

Workup

  1. dissolutiondissolved in the solvent
  2. washThe aqueous phase was washed with more EtOAc
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-31eda029c34f465c90e975136b229a9d
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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