Water → HCID 66591140, compound

HRID 1894800Notes

Reaction equation

HRID 1894800 reaction equation
Br[C:2]1[O:6][C:5]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[C:13]([CH2:22][N-:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=1)(=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]C.[OH2:40].[CH3:41]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>[CH3:41][N:23]([CH2:24][C:25]1[CH:26]=[C:27]([C:2]2[O:6][C:5]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=2)[CH:28]=[CH:29][CH:30]=1)[C:22](=[O:40])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 66591461HCID 66591461, compoundHCID 86618118HCID 86618118, compound

Product 1

HCID 66591140HCID 66591140, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 62657Potassium Phosphate, TribasicSolvent

Conditions

Temperature
80 °C

Procedure

278 mg (1.20 mmol, 1.5 eq) of methyl 3-(5-bromofuran-2-yl)acrylate and 300 mg (0.80 mmol, 1.0 eq) of octanoylmethyl-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]amide (prepared as in 1e) are dissolved in 5 ml of a 5/1 mixture of dimethylformamide and of 2M potassium phosphate solution. 46 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 methyl 3-(5-{3-[(methyloctanoylamino)methyl]phenyl}furan-2-yl)acrylate are obtained. Yield=78%.

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-b65534e879544f9b86472baa5ad0ab58
Source dataset
uspto-grants-2013_08
Patent number
US08513297B2

Reaction notes

Loading…