Hydrochloric Acid → HCID 78324788, compound

HRID 2201917Notes

Reaction equation

Cl.[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.Cl[C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:31])([CH3:30])[C:27]([OH:29])=[O:28])=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>O1CCOCC1.O>[CH3:31][C:26]([C:23]1[CH:24]=[CH:25][C:20]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][N:4]3[CH2:5][CH2:6][CH2:7][C@H:3]3[CH3:2])=[CH:11][CH:12]=2)=[CH:21][CH:22]=1)([CH3:30])[C:27]([OH:29])=[O:28]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of (R)-4-(2-(2-methylpyrrolidin-1-yl)ethyl)phenylboronic acid hydrochloride (50.9 mg, 0.189 mmol), 2-(4-chlorophenyl)-2-methylpropanoic acid (50 mg, 0.252 mmol), Na2CO3 (107 mg, 1.007 mmol), and dichlorobis(p-dimethylaminophenyldi-tert-butylphosphine)palladium (1.782 mg, 2.52 μmol) in 1,4-dioxane (1 mL) and H2O (0.2 mL) was heated under microwave irradiation at 150° C. for 10 min. To the resulting mixture was added 2 M HCl (8 mL) and extracted with 5% EtOAc/hexane (10 mL). To the aqueous phase was added ACN (2 mL) to dissolve the solid precipitates. The mixture was purified by HPLC. LCMS m/z=352.4 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.12 (d, J=13.6 Hz, 0.4H), 1.35 (d, J=6.4 Hz, 2.6H), 1.48 (s, 6H), 1.57-1.72 (m, 1H), 1.89-2.00 (m, 2H), 2.09-2.21 (m, 1H), 2.93-3.11 (m, 4H), 3.22-3.35 (m, 1H), 3.37-3.48 (m, 1H), 3.62-3.75 (m, 1H), 7.27 (d, J=8.1 Hz, 2H), 7.37 (d, J=8.3 Hz, 2H), 7.51 (d, J=8.2 Hz, 2H), 7.52 (d, J=7.9 Hz, 2H).

Workup

extractionextracted with 5% EtOAc/hexane (10 mL)
additionTo the aqueous phase was added ACN (2 mL)
dissolutionto dissolve the solid
customprecipitates
customThe mixture was purified by HPLC

Sources & evidence

ORD record: ord-c73738a2767d45eca9223926d2655cd6
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365511B2

Reaction notes

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