Lithium Chloride → HCID 86680684, compound

HRID 1615447Notes

Reaction equation

HRID 1615447 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Sn](CCCC)(CCCC)CCCC)[N:4]=1.O(P(O[C:39]1[N:40]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41][CH2:42][O:43][CH:44]=1)(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[Cl-].[Li+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[N:4]=[C:5]([C:39]2[N:40]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41][CH2:42][O:43][CH:44]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 105248912-Methoxy-6-(tributylstannyl)pyridineHCID 86680661tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86680684HCID 86680684, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methoxy-6-(tributylstannyl)pyridine (552 mg, 1.39 mmol) and tert-butyl 5-((diphenoxyphosphoryl)oxy)-2H-1,4-oxazine-4(3H)-carboxylate (300 mg, 0.69 mmol) were dissolved in THF (6 ml). Lithium chloride (90 mg, 2.1 mmol) and Pd(PPh3)4 (78 mg, 0.069 mmol) were added and the mixture heated at reflux for 18 hours. The mixture was concentrated and purified on silica gel, eluting with 0-10% ethyl acetate/petrol. This gave the title compound as a brown solid (60 mg, 30%); 1H-NMR (CDCl3) 1.26 (9H, s), 3.77 (2H, t), 3.92 (3H, s), 4.19 (2H, m), 6.55 (1H, d), 6.76 (1H, d), 6.80 (1H, s), 7.49 (1H, t); MS ES(+) 293.2 (M++1); HRMS m/z calcd for C15H20N2O4+H+ 293.1501 [M+H+]. Found 293.1512. IR λmax=1701 cm−1.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 hours
  3. concentrationThe mixture was concentrated
  4. custompurified on silica gel
  5. washeluting with 0-10% ethyl acetate/petrol

Sources & evidence

ORD record
ord-ef03c38240594669a08368544f40b82b
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

Loading…