Triethylamine → 4-(5-Ethoxycarbonylmethyl-2-methoxy-phenoxy)-3-isopropylsulfanylmethyl-benzoic acid methyl ester

HRID 888495Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][C:16]=2[CH2:22][S:23][CH:24]([CH3:26])[CH3:25])[CH:7]=1)[CH3:2].C(N(CC)CC)C>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:3][C:4](=[O:27])[C:18]1[CH:19]=[CH:20][C:15]([O:14][C:8]2[CH:7]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:27])[CH:11]=[CH:10][C:9]=2[O:12][CH3:13])=[C:16]([CH2:22][S:23][CH:24]([CH3:26])[CH3:25])[CH:17]=1

Participants

Conditions

Temperature: 65 °C

Procedure

[3-(4-Bromo-2-isopropylsulfanylmethyl-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester (0.5 g, 1.1 mmol) and triethylamine (0.5 mL) were dissolved in DMF (10 mL) and MeOH (10 mL) and degassed for 10 minutes with N2. [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.09 g, 0.11 mmol) was added, and then carbon monoxide was bubbled through the solution for 10 minutes. The reaction was stirred under a balloon of carbon monoxide at 65° C. overnight, and then concentrated and purified by silica gel chromatography to give the title compound.

Workup

customMeOH (10 mL) and degassed for 10 minutes with N2
customcarbon monoxide was bubbled through the solution for 10 minutes
concentrationconcentrated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-5232bce9e0344484adbad271023671e7
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247602B2

Reaction notes

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