Potassium Carbonate → HCID 178482039, compound

HRID 2362591Notes

Reaction equation

HRID 2362591 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([CH3:16])[CH2:13][O:12][N:11]([CH3:14])[C:10](=[NH:15])[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[C:17]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)#[N:18].C([O-])([O-])=O.[K+].[K+]>C(O)C>[C:17]([C:19]1[CH:24]=[C:23]([C:2]2[CH:3]=[C:4]([C:8]3([CH3:16])[CH2:13][O:12][N:11]([CH3:14])[C:10](=[NH:15])[NH:9]3)[CH:5]=[CH:6][CH:7]=2)[CH:22]=[CH:21][CH:20]=1)#[N:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 178482038HCID 178482038, compound

Product 1

HCID 178482039HCID 178482039, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(3-bromophenyl)-2,5-dimethyl-1,2,4-oxadiazinan-3-imine (DC7; R6=Me, R1=Me) (0.025 g, 0.088 mmol, 1 eq), 3-cyanophenylboronic acid (0.019 g, 0.13 mmol, 1.5 eq), FibreCat (40 mg), anhydrous ethanol (1.5 mL), and a 1N K2CO3 aqueous solution (0.12 mL, 0.12 mmol, 1.4 eq) in a microwave vial was heated in a microwave reactor (Emrys Optimizer) at 110° C. for 15 min. The mixture was filtered, concentrated and purified by prep HPLC (B) to give 0.012 g (44%) of 5-(3-(3-cyanophenyl)phenyl)-2,5-dimethyl-1,2,4-oxadiazinan-3-imine (DC8; R6=Me, R1=Me, R21=3-cyanophenyl) as a white solid. 1H NMR (CDCl3) 10.67 (s, 1H), 8.05 (br s, 1H), 7.85 (m, 2H), 7.50-7.66 (m, 5H), 7.35 (m, 1H), 4.22 (dd, J1=11.8 Hz, J2=48.6 Hz, 2H), 3.40 (s, 3H), 1.76 (s, 3H). MS m/e 307.3 (M+H)

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. custompurified by prep HPLC (B)

Sources & evidence

ORD record
ord-b1549e8a953841c9aed90d6fd381b9a9
Source dataset
uspto-grants-2014_04
Patent number
US08691833B2

Reaction notes

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