Dimethylformamide → Methyl 2-(1-cycloocten-1-yl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662394Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1I.CN(C=O)C.[C:26]1(B2OC(C)(C)C(C)(C)O2)=[CH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1.C(=O)([O-])[O-].[K+].[K+]>[Cl-].[Na+].O.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>[C:26]1([C:11]2[CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[CH:15][C:10]=2[C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[F:1])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of 66.15D (0.750 g, 1.9 mmol) in DMF (4.00 mL, 52 mmol) at 23° C. was added (Z)-2-cyclooctenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 66.16C (0.92 g, 3.9 mmol), potassium carbonate (0.81 g, 5.8 mmol), and then tetrakis(triphenylphosphine)palladium (0.22 g, 0.19 mmol). The mixture was heated at 90° C. for 19 hours and then cooled to room temperature. The reaction was diluted with brine and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was purified on silica gel (0-10% EtOAc in hexanes) to yield 66.16D as a colorless oil (0.35 g, 49% yield).

Workup

temperaturecooled to room temperature
extractionextracted three times with EtOAc
dry with materialAfter drying over anhydrous magnesium sulfate
filtrationfiltering
customthe organic solvent was removed under reduced pressure
customthe product was purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-9d0c29575ed64eddb75d4dfa12b680f9
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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