Water → HCID 68530937, compound

HRID 644218Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:3]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC.C(OCC)(=O)C>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][CH:13]([O:12][C:4]2[CH:3]=[C:2]([C:30]3[CH:31]=[CH:32][C:27]([Cl:26])=[CH:28][CH:29]=3)[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])[CH2:14][CH2:15]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 4-bromo-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-benzoate (0.207 g, 0.5 mmol) in 1,2-dimethoxyethane (3 mL) was added 4-chlorophenyl-boronic acid (0.094 g, 0.6 mmol), tetrakis(triphenylphospine)palladium(0) (0.010 g), and 1 M aq potassium phosphate (0.8 mL). The reaction mixture was heated at 80° C. overnight under a nitrogen atmosphere. The reaction was then cooled to room temperature and water (10 mL) and ethyl acetate (50 mL) were added. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×25 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by RPHPLC (ethyl acetate/hexane 1:4) to give 0.190 g (85%) of product.

Workup

temperatureThe reaction was then cooled to room temperature
customThe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate (2×25 mL)
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by RPHPLC (ethyl acetate/hexane 1:4)

Sources & evidence

ORD record: ord-a980e54304c14ca2b702a7ee7afad467
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700628B2

Reaction notes

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