1,2-Dimethoxyethane → HCID 68718646, compound

HRID 1397484Notes

Reaction equation

I[C:2]1[S:6][C:5]([C:7]2([OH:13])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[N:4][CH:3]=1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)([O-:16])=[O:15].[F-].[K+].C(COC)OC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([C:2]2[S:6][C:5]([C:7]3([OH:13])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]3)=[N:4][CH:3]=2)=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of Example 1B (1.0 g, 3.2 mmol), 4-nitrophenylboronic acid (0.75 g, 4.5 mmol), KF (0.56 g, 9.6 mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.22 g, 0.32 mmol) in a solvent mixture of dimethoxyethane (5 mL) and methanol (5 mL) was heated to 90° C. for 16 h. The reaction was cooled to room temperature and partitioned between ethyl acetate (10 mL) and H2O (10 mL). The layers were separated, and the aqueous was extracted with additional ethyl acetate (2×10 mL). The combined organics were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 gel, eluting with 50% ethyl acetate in hexane; to give the title compound. MS (ESI) m/z 307 [M+H]+.

Workup

temperatureThe reaction was cooled to room temperature
custompartitioned between ethyl acetate (10 mL) and H2O (10 mL)
customThe layers were separated
extractionthe aqueous was extracted with additional ethyl acetate (2×10 mL)
dry with materialThe combined organics were dried with anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on SiO2 gel
washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-973722dcd0eb4bbca58e4c6a58d79226
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901152B2

Reaction notes

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