Water → HCID 66591074, compound

HRID 1894805Notes

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]([CH2:33][CH2:34][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+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:42][N:11]([CH2:12][C:13]1[S:14][CH:15]=[C:16]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][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

Conditions

Temperature: 90 °C

Procedure

430 mg (1.29 mmol, 1 eq) of octanoyl(4-bromothiophen-2-ylmethyl)methylamide and 470 mg (1.55 mmol, 1.2 eq) of ethyl 3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]propanoate are dissolved in 4 ml of a 6/1 mixture of dimethylformamide and of 2M potassium phosphate solution. 15 mg (0.064 mmol, 5 mol %) of palladium acetate and 45 mg (0.129 mmol, 10 mol %) of dicyclohexyl 2-biphenylphosphine are added. The mixture is stirred for 2 hours at 90° 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 70/30 heptane/ethyl acetate). 245 mg of ethyl 3-(4-{5-[(methyloctanoylamino)methyl]thiophen-3-yl}phenyl)propanoate are obtained. Yield=44%.

Workup

extractionis then extracted with ethyl acetate
dry with materialdried over sodium sulfate
customThe solvents are evaporated off
customthe residue is then chromatographed on silica gel (80/20 to 70/30 heptane/ethyl acetate)

Sources & evidence

ORD record: ord-b07b6bdc0676481b9550952e04a4a53f
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513297B2

Reaction notes

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