Potassium Phosphate, Tribasic → Tert-butyl 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoate

HRID 1694830Notes

Reaction equation

HRID 1694830 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([CH2:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:26])=[O:23])=[CH:17][CH:16]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>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(C)C=CC=CC=1>[NH:21]([C:22](=[O:23])[CH:24]([C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1)[C:25]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26])[C:18]1[CH:17]=[CH:16][CH:15]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 69298Propanediamide, N,N'-diphenyl-HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 11334366Tert-butyl 4-bromobenzoate

Product 1

HCID 59376446Tert-butyl 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of tert-butyl 4-bromobenzoate (7.349 g, 28.6 mmol), malondianilide (6.01 g, 23.7 mmol), and K3PO4 (15.15 g, 71 mmol) was added Pd2(dba)3 (996 mg, 1.09 mmol), toluene (50 mL), and P(tert-Bu)3 (1.08 mL, 4.35 mmol). The reaction mixture was degassed and heated to 70° C. for 16 h, additional Pd[P(tert-Bu)3]2 was added and the reaction was heated to 80° C. After 24 h, the reaction mixture was diluted with ethyl acetate, washed with water (1×), brine (1×), dried over MgSO4, and concentrated. tert-Butyl 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoate was used without further purification: ESIMS calcd 431.2 (M++H), found 431.1 (M++H).

Workup

  1. customThe reaction mixture was degassed
  2. additionadditional Pd[P(tert-Bu)3]2 was added
  3. temperaturethe reaction was heated to 80° C
  4. additionthe reaction mixture was diluted with ethyl acetate
  5. washwashed with water (1×), brine (1×)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customtert-Butyl 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoate was used without further purification

Sources & evidence

ORD record
ord-964ce9a535e146d495695875ee636987
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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