Water → HCID 57421271, compound

HRID 333826Notes

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-aff68c328b1349298c1858c99502e433
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883786B2

Reaction notes

Loading…