Water → HCID 66591402, compound

HRID 1894796Notes

Reaction equation

Br[C:2]1[S: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[S: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

Conditions

Temperature: 80 °C

Procedure

200 mg (0.81 mmol, 1.0 eq) of methyl 3-(5-bromothiophen-2-yl)acrylate and 334 mg (0.89 mmol, 1.1 eq) of octanoylmethyl-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]amide are dissolved in 5 ml of a 5/1 mixture of dimethylformamide and of 2M potassium phosphate solution. 93 mg (0.08 mmol, 10 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). 220 mg of methyl 3-(5-{3-[(methyloctanoylamino)methyl]phenyl}thiophen-2-yl)acrylate are obtained. Yield=65%.

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 60/40 heptane/ethyl acetate)

Sources & evidence

ORD record: ord-86b352cedaa2484b8ed2e060033a944b
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513297B2

Reaction notes

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