Sodium Carbonate → 4-[5-(1-Morpholin-4-yl-ethyl)-furan-2-yl]-benzoic acid

HRID 606575Notes

Reaction equation

Br[C:2]1[O:6][C:5]([CH:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH3:8])=[CH:4][CH:3]=1.C(C[C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)(O)=O.[C:28]([O-:31])([O-])=[O:29].[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.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>[N:9]1([CH:7]([C:5]2[O:6][C:2]([C:19]3[CH:24]=[CH:23][C:22]([C:28]([OH:31])=[O:29])=[CH:21][CH:20]=3)=[CH:3][CH:4]=2)[CH3:8])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: 70 °C

Procedure

4-[1-(5-bromo-furan-2-yl)-ethyl]-morpholine (0.54 mmol) was taken up in 7 ml toluene and 4-carboxymethylphenylboronic acid (0.54 mmol) was added as a solution in 0.7 ml of EtOH. 12 mi of 2M aqueous Na2CO3 solution was added, followed by Pd(PPh3)4 (0.054 mmol). Reaction was stirred at 70° C. for 17 h under a nitrogen atmosphere and then cooled to room temperature and extracted with DCM (×2). Combined organic layers were washed with brine, concentrated in vacuo and the residue purified by flash chromatography (silica, 20-50% EtOAc in hexane). This fumished the pure 4-[5-(1-Morpholin-4-yl-ethyl)-furan-2-yl]-benzoic acid methyl ester as a powdery grey solid: m/z in MS ES+=316 [M+H]+, 0.08 mmol, 15% yield.

Workup

customReaction
temperaturecooled to room temperature
extractionextracted with DCM (×2)
washCombined organic layers were washed with brine
concentrationconcentrated in vacuo
customthe residue purified by flash chromatography (silica, 20-50% EtOAc in hexane)

Sources & evidence

ORD record: ord-b6224f56946749a5b97da17335915666
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915300B2

Reaction notes

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