Cesium fluoride → Methyl 2'-fluoro-5'-(methyloxy)-2-(tetrahydro-2H-pyran-2-yloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662340

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1B(O)O.[F-].[Cs+].Br[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1>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.COCCOC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a 2 dram vial charged with 2-fluoro-5-methoxyphenylboronic acid (available from Aldrich) (3.17 g, 18.7 mmol), tetrakis(triphenylphosphine)palladium (0) (0.719 g, 0.622 mmol), cesium fluoride (1.15 mL, 31.1 mmol), and 26.2 (1.96 g, 6.22 mmol), was added DME (20 mL). The reaction mixture was then heated at 90° C. overnight. The reaction was allowed to cool and then filtered and concentrated. The crude product was purified by combiflash (0 to 10% EtOAc/hexanes) yielding 26.3 (1.61 g, 71.8% yield).

Workup

temperatureto cool
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by combiflash (0 to 10% EtOAc/hexanes)

Sources & evidence

ORD record: ord-72bfed00d73443308d9f04a6536efbb6
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Linked notes

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