HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → HCID 89657570, compound

HRID 1775200
Notes
Print preview

Reaction equation

HRID 1775200 reaction equation
Br[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[CH2:14][N:15]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:16][C:17](=[O:19])[CH:18]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C(Cl)Cl.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:19]=[C:17]1[C:18]2[C:2]3[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=3[NH:12][C:13]=2[CH2:14][N:15]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:16]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 89655469HCID 89655469, compound

Product 1

HCID 89657570HCID 89657570, compoundYield 72%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalyst
HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent
HCID 6344DichloromethaneSolvent

Procedure

A mixture of benzyl 3-((2-bromo-3-(methoxycarbonyl)phenyl)amino)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (0.13 g, 0.28 mmol), palladium acetate (0.013 g, 0.06 mmol), tri-o-tolylphosphine (0.72 g, 0.19 mmol), and triethylamine (0.36 g, 0.36 mmol) in acetonitrile (2 mL) was heated in a sealed tubule flushed with nitrogen at 100° C. for 9 h. The cooled reaction mixture was diluted with DCM (3×50 mL) and water (10 mL). The organic layer was separated, washed with water, dried (Na2SO4), and concentrated. The remaining residue was chromatographed on silica gel, eluted with gradient 0-100% EtOAc in hexane to give the title compound (0.076 g, 72%). 1H NMR (CDCl3-d1) δ 9.62 (s, 1H), 7.24-7.50 (m, 8H), 5.18 (s, 2H), 4.88 (s, 2H), 4.27 (s, 2H), 3.98 (s, 3H). MS (ESI) m/e [M+1]+ 379.0.

Workup

  1. temperaturewas heated in a sealed
  2. customtubule flushed with nitrogen at 100° C. for 9 h
  3. customThe cooled reaction mixture
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe remaining residue was chromatographed on silica gel
  9. washeluted with gradient 0-100% EtOAc in hexane

Sources & evidence

ORD record
ord-8771289ab66e4be3af5afad683c28e2b
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09260440B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes