Potassium Phosphate, Tribasic → methyl(E)-3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]acrylate

HRID 250845Notes

Reaction equation

HRID 250845 reaction equation
C([O:8][C:9]1[CH:10]=[C:11](/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])[CH:12]=[CH:13][C:14]=1I)C1C=CC=CC=1.[CH2:22]([NH:29][C:30](=[O:48])[N:31]([CH3:47])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[CH2:22]([NH:29][C:30](=[O:48])[N:31]([C:32]1[CH:37]=[C:36]([C:14]2[CH:13]=[CH:12][C:11](/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])=[CH:10][C:9]=2[OH:8])[CH:35]=[CH:34][CH:33]=1)[CH3:47])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 595749253-Heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]ureaHCID 66971542methyl(E)-3-(3-benzyloxy-4-iodophenyl)acrylate

Product 1

HCID 67273468methyl(E)-3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]acrylateYield 118.9%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4.6 g (11.67 mmol, 1 eq) of methyl (E)-3-(3-benzyloxy-4-iodophenyl)acrylate, 4.8 g (12.83 mmol, 1.1 eq) of 3-heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]urea (prepared as in Example 1e) in 18 ml of dimethylformamide+3 mL of 2M potassium phosphate solution, in the presence of 128 mg (5 mol %) of palladium acetate and 408 mg (10 mol %) of 2-(dicyclohexylphosphino)biphenyl is stirred at 80° C. for 5 hours. The reaction medium is hydrolyzed in water and then extracted with ethyl acetate. The organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. The solvents are evaporated off and the oil obtained is chromatographed on silica (7/3 heptane/ethyl acetate). 5.89 g of methyl (E)-3-[3′-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]acrylate are obtained in oil form. Yield=98%

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvents are evaporated off
  5. customthe oil obtained
  6. customis chromatographed on silica (7/3 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-bc61e1b7bd4c47ae861b21ec2cbae203
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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