Potassium Phosphate, Tribasic → HCID 178475809, compound

HRID 593074Notes

Reaction equation

HRID 593074 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7]2[C:8](=[O:15])[N:9]([CH3:14])[CH:10]=[C:11](Br)[CH:12]=2)=[N:2]1.[C:16]([O:19][CH2:20][C:21]1[C:22]([N:30]2[CH2:41][CH2:40][N:39]3[C:32](=[CH:33][C:34]4[CH2:35][C:36]([CH3:43])([CH3:42])[CH2:37][C:38]=43)[C:31]2=[O:44])=[N:23][CH:24]=[CH:25][C:26]=1B(O)O)(=[O:18])[CH3:17].[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>[C:16]([O:19][CH2:20][C:21]1[C:22]([N:30]2[CH2:41][CH2:40][N:39]3[C:32](=[CH:33][C:34]4[CH2:35][C:36]([CH3:43])([CH3:42])[CH2:37][C:38]=43)[C:31]2=[O:44])=[N:23][CH:24]=[CH:25][C:26]=1[C:11]1[CH:12]=[C:7]([NH:6][C:3]2[CH:4]=[CH:5][NH:1][N:2]=2)[C:8](=[O:15])[N:9]([CH3:14])[CH:10]=1)(=[O:18])[CH3:17]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 517045Sodium AcetateHCID 86684340[4-(Dihydroxyboranyl)-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-3-yl]methyl acetateHCID 178479985HCID 178479985, compound

Product 1

HCID 178475809HCID 178475809, compoundYield 38%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
90 °C

Procedure

A 50-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 289b (200 mg, 0.74 mmol), (2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-{3-[(acetoxy)methyl]-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-4-yl}boronic acid 199e (360 mg, 0.90 mmol), PdCl2(dppf) (41 mg, 0.050 mmol), K3PO4 (320 mg, 1.5 mmol), sodium acetate (123 mg, 1.5 mmol), acetonitrile (10 mL), and water (0.2 mL). The system was evacuated and then refilled with N2. Then it was heated at 90° C. for 4 h. The mixture was 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 10:1 dichloromethane/methanol to afford 289c as a pale yellow solid (150 mg, 38%). MS-ESI: [M+H]+ 542.3.

Workup

  1. customA 50-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customThe system was evacuated
  3. additionrefilled with N2
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica-gel column chromatography
  8. washeluting with 10:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-2916ead698ed4c7ab6fd641227482634
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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