Dichloromethane → HCID 57423921, compound

HRID 2064081Notes

Reaction equation

HRID 2064081 reaction equation
CC(C)([O-])C.[Na+].[F:7][CH:8]([F:34])[O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[O:18])=[C:12](I)[CH:11]=1.ClCCl>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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:7][CH:8]([F:34])[O:9][C:10]1[CH:15]=[CH:14][C:13]2[NH:16][C:17](=[O:18])[N:19]([CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)[C:12]=2[CH:11]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 23676156Sodium t-butoxideHCID 59863024HCID 59863024, compound

Product 1

HCID 57423921HCID 57423921, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of tris(dibenzylideneacetone)dipalladium (0) (0.18 g), 1,1′-bis(diphenylphosphino)ferrocene (0.10 g), sodium tert-butoxide (0.6 g) in 1,4-dioxane (10 ml) was stirred under an atmosphere of argon for 10 minutes. 1,1-Dimethylethyl 4-{[({4-[(difluoromethyl)oxy]-2-iodophenyl}amino)carbonyl]amino}-1-piperidinecarboxylate (D52, 1.3 g) was added and the mixture was heated to 90° C. The mixture was stirred at this temperature overnight. The mixture was poured into dichloromethane which was washed with water and brine. The solvent was removed and the residue was chromatographed on silica gel eluted with ethyl acetate/hexane 0-50% to give the title compound as a off-white solid. (0.54 g).

Workup

  1. washwas washed with water and brine
  2. customThe solvent was removed
  3. customthe residue was chromatographed on silica gel
  4. washeluted with ethyl acetate/hexane 0-50%

Sources & evidence

ORD record
ord-a505bc2b45b1438391c4cb19371628c7
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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