Dichloromethane → HCID 66741150, compound

HRID 2064067Notes

Reaction equation

HRID 2064067 reaction equation
CC(C)([O-])C.[Na+].Br[C:8]1[CH:13]=[C:12]([O:14][C:15]([F:18])([F:17])[F:16])[CH:11]=[CH:10][C:9]=1[NH:19][C:20]([NH:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)=[O:21].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]>[O:21]=[C:20]1[N:22]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)[C:8]2[CH:13]=[C:12]([O:14][C:15]([F:18])([F:17])[F:16])[CH:11]=[CH:10][C:9]=2[NH:19]1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 23676156Sodium t-butoxideHCID 57423911HCID 57423911, compound

Product 1

HCID 66741150HCID 66741150, 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) (0.33 g), 1,1′-bis(diphenylphosphino)ferrocene (0.21 g), sodium tert-butoxide (1.1 g) in 1,4-dioxane (20 mL) was stirred under an atmosphere of argon for 10 minutes. 1,1-Dimethylethyl 4-{[({2-bromo-4-[(trifluoromethyl)oxy]phenyl}amino)carbonyl]amino}-1-piperidinecarboxylate (D30) (2.7 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 dilute ammonium chloride, brine and dried over sodium sulphate. 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 solid foam. (1.54 g)

Workup

  1. washwas washed with dilute ammonium chloride, brine
  2. dry with materialdried over sodium sulphate
  3. customThe solvent was removed
  4. customthe residue was chromatographed on silica gel
  5. washeluted with ethyl acetate/hexane 0-50%

Sources & evidence

ORD record
ord-5586bb01ca034f3797fab3ea29f75f7e
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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