Sodium Carbonate → HCID 178461410, compound

HRID 2201943Notes

Reaction equation

HRID 2201943 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:31]=[CH:30][C:23]([CH2:24][C:25]2[NH:29][N:28]=[N:27][N:26]=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][C:25]3[NH:29][N:28]=[N:27][N:26]=3)=[CH:30][CH:31]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 68728719HCID 68728719, compoundHCID 178419386HCID 178419386, compound

Product 1

HCID 178461410HCID 178461410, 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-bromobenzyl)-1H-tetrazole (53.2 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. The residue was purified by HPLC to give the title compound. LCMS m/z=348.1 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.27 (d, J=6.5 Hz, 0.4H), 1.46 (d, J=6.6 Hz, 2.6H), 1.70-1.82 (m, 1H), 2.02-2.11 (m, 2H), 2.22-2.33 (m, 1H), 3.05-3.21 (m, 4H), 3.36-3.48 (m, 1H), 3.52-3.62 (m, 1H), 3.72-3.83 (m, 1H), 4.36 (s, 2H), 7.36-7.44 (m, 4H), 7.61-7.67 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-3cb5e1b739694b5187a16e8fc3f086a1
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

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