Water → HCID 76286162, compound

HRID 2201950Notes

Reaction equation

Br[C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[CH3:13])=[CH:4][CH:3]=1.B([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:21][CH:20]=1)(O)O.C([O-])([O-])=O.[Na+].[Na+].O>C(#N)C.CN(C=O)C.CO>[CH3:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[CH2:7][CH2:6][C:5]1[CH:14]=[CH:15][C:2]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:21][CH:20]=2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

In a microwave reaction vial was added (R)-1-(4-bromophenethyl)-2-methylpyrrolidine (200 mg, 0.746 mmol), 3-(4-boronophenyl)propanoic acid (289 mg, 1.491 mmol), Na2CO3 (395 mg, 3.73 mmol), dihydrogen dichlorobis(di-tert-butylphosphinito-kP)palladate (POPd) (11.23 mg, 0.022 mmol) and a mixture of H2O (0.4 mL), MeOH (0.6 mL), and DMF (2.0 mL). The reaction mixture was heated under microwave irradiation at 150° C. for 15 min. To the mixture was added acetonitrile (20 mL) and filtered. The filtrate was concentrated and the residue was purified by HPLC to give the title compound. LCMS m/z=338.2 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.24 (d, J=14.9 Hz, 0.5H), 1.46 (d, J=6.3 Hz, 2.5H), 1.72-1.84 (m, 1H), 2.01-2.15 (m, 2H), 2.20-2.32 (m, 1H), 2.66 (t, J=7.5 Hz, 2H), 2.96 (t, J=7.5 Hz, 2H), 3.02-3.20 (m, 4H), 3.33-3.46 (m, 1H), 3.48-3.62 (m, 1H), 3.75-3.86 (m, 1H), 7.34 (d, J=8.2 Hz, 2H), 7.39 (d, J=8.2 Hz, 2H), 7.58 (d, J=8.2 Hz, 2H), 7.63 (d, J=8.2 Hz, 2H).

Workup

customIn a microwave reaction
filtrationfiltered
concentrationThe filtrate was concentrated
customthe residue was purified by HPLC

Sources & evidence

ORD record: ord-327c722f90a6421bacb48bc5628c959d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365511B2

Reaction notes

Loading…