Dimethylformamide → HCID 86223665, compound

HRID 250882Notes

Reaction equation

HRID 250882 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]([CH2:19][CH2:20][CH3:21])[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)=[O:23].CN(C)C=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O>[CH2:19]([N:8]([C:4]1[CH:3]=[C:2]([C:27]2[CH:28]=[CH:29][C:24]([CH:22]=[O:23])=[CH:25][CH:26]=2)[CH:7]=[CH:6][CH:5]=1)[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:10])[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 5910734-Formylphenylboronic AcidHCID 67272875HCID 67272875, compound

Product 1

HCID 86223665HCID 86223665, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

135 mg (5 mol %) of tetrakis(triphenyl-phosphine)palladium are added to a solution of 830 mg (2.34 mmol, 1 eq) of 1-(3-bromophenyl)-1-propyl-3-heptylurea and 460 mg (3.0 mmol, 1.3 eq) of 4-formylphenylboronic acid in 10 mL of a mixture of dimethylformamide and of 2M potassium phosphate solution (8/2). The reaction mixture is stirred for 3 hours at 90° C. The reaction is stopped by addition of 50 mL of water and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 735 mg of 1-propyl-1-(4′-formylbiphenyl-3-yl)-3-heptylurea are obtained in oil form. Yield=82%

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-bbe26387cffc48f8a17addae765c83e4
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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