Water → HCID 57421271, compound

HRID 1097927Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:24])[C:11]([C:17]1[CH:22]=[CH:21][N:20]=[C:19](I)[CH:18]=1)([OH:16])[C:12]([F:15])([F:14])[F:13].[CH2:25]([O:27][C:28]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)=[O:29])[CH3:26].O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C(OCC)(=O)C>[CH2:25]([O:27][C:28](=[O:29])[C:30]1[CH:35]=[CH:34][C:33]([C:19]2[CH:18]=[C:17]([C:11]([OH:16])([C:12]([F:15])([F:14])[F:13])[CH:10]([C:3]3[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=3[Cl:1])[CH3:24])[CH:22]=[CH:21][N:20]=2)=[CH:32][CH:31]=1)[CH3:26]

Participants

Conditions

Temperature: 80 °C

Procedure

3-(2-Chloro-4-methoxy-phenyl)-1,1,1-trifluoro-2-(2-iodo-pyridin-4-yl)-butan-2-ol (Example 139, 92 mg), 4-ethoxycarbonylphenylboronic acid (42 mg) and 1,1,bis(diphenylphosphino)ferrocenpalladium(II)dichloromethane in dioxane (0.7 mL) was treated with water (0.4 mL) and 2N—Na2CO3 (0.351 mL) and stirred at 80° C. under argon for 16 h. The reaction mixture was cooled down to r.t., diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (10 g silica gel, ethyl acetate/heptane 1:2) to give the title compound as light yellow amorphous material (78 mg). MS (m/e)=494.2 (MH+).

Workup

temperatureThe reaction mixture was cooled down to r.t.
washwashed with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (10 g silica gel, ethyl acetate/heptane 1:2)

Sources & evidence

ORD record: ord-f76f96d57c8c4e64a9040a7244a699ad
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143280B2

Reaction notes

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