Water → HCID 66591532, compound

HRID 1894802Notes

Reaction equation

HRID 1894802 reaction equation
[C:1]([CH2:10][N-:11][CH2:12][C:13]1[S:14][CH:15]=[C:16](Br)[CH:17]=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]C.CC1(C)C(C)(C)OB([C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:29][CH:28]=2)O1.[OH2:41].[CH3:42]N(C)C=O>P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:42][N:11]([CH2:12][C:13]1[S:14][CH:15]=[C:16]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:29][CH:28]=2)[CH:17]=1)[C:10](=[O:41])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 66591357HCID 66591357, compoundHCID 86618120HCID 86618120, compound

Product 1

HCID 66591532HCID 66591532, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 62657Potassium Phosphate, TribasicSolvent

Conditions

Temperature
80 °C

Procedure

300 mg (0.90 mmol, 1.0 eq) of octanoyl(4-bromothiophen-2-ylmethyl)methylamide and 326 mg (1.08 mmol, 1.2 eq) of ethyl 3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]acrylate are dissolved in 4 ml of a 5/1 mixture of dimethylformamide and of 2M potassium phosphate solution. 52 mg (0.04 mmol, 5 mol %) of tetrakis(triphenylphosphine)palladium are added and the reaction mixture is then stirred for 2 hours at 80° C. The reaction is stopped by adding 30 mL of water and is 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 (80/20 to 60/40 heptane/ethyl acetate). 250 mg of ethyl 3-(4-{5-[(methyloctanoylamino)methyl]thiophen-3-yl}phenyl)acrylate are obtained. Yield=65%.

Workup

  1. extractionis then extracted 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 (80/20 to 60/40 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-21710f6eff1848d5b9e6cd33cc0dba14
Source dataset
uspto-grants-2013_08
Patent number
US08513297B2

Reaction notes

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