Methyl 3-[3-fluoro-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]acrylate → Methyl 3-[3-fluoro-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate

HRID 250823Notes

Reaction equation

HRID 250823 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]([CH3:31])[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:22])[CH:15]=2)[CH:5]=[CH:6][C:7]=1[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[O:11]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]([CH3:31])[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:22])[CH:15]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 1

HCID 67271956Methyl 3-[3-fluoro-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]acrylate

Product 1

HCID 67272686Methyl 3-[3-fluoro-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoateYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 138 mg (0.32 mmol) of methyl 3-[3-fluoro-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]acrylate in 3 ml of methanol is stirred for 4 hours at room temperature in the presence of 10 mg of 10% Pd/C under a hydrogen atmosphere. The palladium is filtered off and the solvents are evaporated off. The residue is chromatographed on silica gel (70/30 heptane/ethyl acetate). 130 mg of methyl 3-[3-fluoro-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate are obtained. Yield=94%

Workup

  1. filtrationThe palladium is filtered off
  2. customthe solvents are evaporated off
  3. customThe residue is chromatographed on silica gel (70/30 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-13f2f7d23d544d4f8b09bf9be624d45f
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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