Potassium Phosphate, Tribasic → HCID 86684608, compound

HRID 593181Notes

Reaction equation

HRID 593181 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([NH:10][C:11]2[C:12](=[O:27])[N:13]([CH3:26])[CH:14]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:16]=2)[CH:5]=1.Cl[C:29]1[C:34]([CH:35]=[O:36])=[C:33]([N:37]2[CH2:49][CH2:48][C:47]3[N:46]4[C:41]([CH2:42][CH2:43][CH2:44][CH2:45]4)=[CH:40][C:39]=3[C:38]2=[O:50])[N:32]=[CH:31][CH:30]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C([O-])(=O)C.[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.C(#N)C>[CH3:1][O:2][CH2:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([NH:10][C:11]2[C:12](=[O:27])[N:13]([CH3:26])[CH:14]=[C:15]([C:29]3[C:34]([CH:35]=[O:36])=[C:33]([N:37]4[CH2:49][CH2:48][C:47]5[N:46]6[C:41]([CH2:42][CH2:43][CH2:44][CH2:45]6)=[CH:40][C:39]=5[C:38]4=[O:50])[N:32]=[CH:31][CH:30]=3)[CH:16]=2)[CH:5]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 517045Sodium AcetateHCID 866842464-Chloro-2-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)nicotinaldehydeHCID 86684607HCID 86684607, compound

Product 1

HCID 86684608HCID 86684608, compoundYield 22.5%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
95 °C

Procedure

A 50-mL round-bottomed flask equipped with a reflux condenser was charged with 336d (368 mg, 0.98 mmol), 4-chloro-2-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)nicotinaldehyde 139a (270 mg, 0.82 mmol), PdCl2(dppf) (60 mg, 0.082 mmol), K3PO4 (348 mg, 1.64 mmol)), sodium acetate (135 mg, 1.65 mmol), acetonitrile (15 mL), and water (0.5 mL). The system was subjected to three cycles of vacuum/nitrogen flush and heated at 95° C. for 3 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 20:1 ethyl acetate/methanol to afford 336e (100 mg, 22%). MS-ESI: [M+H]+ 542.2

Workup

  1. customA 50-mL round-bottomed flask equipped with a reflux condenser
  2. customflush
  3. temperatureIt was then cooled to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica-gel column chromatography
  7. washeluting with 20:1 ethyl acetate/methanol

Sources & evidence

ORD record
ord-ac290f5f4334476eae45855765d5fba6
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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