Sodium Carbonate → HCID 178461411, compound

HRID 2201944Notes

Reaction equation

HRID 2201944 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.Br[C:20]1[CH:32]=[CH:31][C:23]([CH2:24][CH2:25][C:26]2[NH:30][N:29]=[N:28][N:27]=2)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[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]([C:20]2[CH:21]=[CH:22][C:23]([CH2:24][CH2:25][C:26]3[NH:30][N:29]=[N:28][N:27]=3)=[CH:31][CH:32]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 68728719HCID 68728719, compoundHCID 178419388HCID 178419388, compound

Product 1

HCID 178461411HCID 178461411, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (R)-4-(2-(2-methylpyrrolidin-1-yl)ethyl)phenylboronic acid hydrochloride (50 mg, 0.185 mmol), 5-(4-bromophenethyl)-1H-tetrazole (56.3 mg, 0.223 mmol), Na2CO3 (79 mg, 0.742 mmol), and dichlorobis(p-dimethylaminophenyldi-tert-butylphosphine)palladium (1.313 mg, 1.855 μmol) in 1,4-dioxane (1 mL) and H2O (0.2 mL) was heated under microwave irradiation at 130° C. for 120 min. The mixture was concentrated and the residue was purified by HPLC to give the title compound. LCMS m/z=362.5 [M+H]+; 1.22-1.31 (m, 0.4H), 1.45 (d, J=6.6 Hz, 2.6H), 1.69-1.82 (m, 1H), 2.00-2.10 (m, 2H), 2.21-2.32 (m, 1H), 3.04-3.20 (m, 6H), 3.25-3.31 (m, 2H), 3.35-3.47 (m, 1H), 3.50-3.60 (m, 1H), 3.72-3.83 (m, 1H), 7.31 (d, J=8.1 Hz, 2H), 7.37 (d, J=8.1 Hz, 2H), 7.56 (d, J=8.2 Hz, 2H), 7.61 (d, J=8.2 Hz, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-3facaefab3d34d8b931379fe07196d03
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

Loading…