Water → HCID 66591074, compound

HRID 1092268Notes

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-9c351496536344738e7aba202e336939
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129416B2

Reaction notes

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