Potassium Phosphate, Tribasic → HCID 90333923, compound

HRID 595708Notes

Reaction equation

HRID 595708 reaction equation
Br[C:2]1[C:3](=[O:9])[NH:4][NH:5][C:6](=[O:8])[CH:7]=1.[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14](B(O)O)[NH:15]2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.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]>[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([C:2]1[C:3](=[O:9])[NH:4][NH:5][C:6](=[O:8])[CH:7]=1)[NH:15]2

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2549424-Bromopyridazine-3,6-diolHCID 90333436HCID 90333436, compound

Product 1

HCID 90333923HCID 90333923, compoundYield 40.8%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a degassed solution of 4-bromo-1,2-dihydropyridazine-3,6-dione (100 mg, 0.5 mmol), (4-fluoro-1H-indol-2-yl)boronic acid (131 mg, 0.7 mmol) and K3PO4 (279 mg, 1.1 mmol) in DMF (2 mL) and H2O (0.2 mL) was added Pd(dppf)Cl2 (5 mg) under N2. The mixture was stirred at 80° C. for 12 h. After the solvent was removed, the residue was purified by prep-TLC (DCM:EtOAc=10:1) to give the product of 4-(4-fluoro-1H-indol-2-yl)-1,2-dihydropyridazine-3,6-dione (50 mg, yield: 39%). 1H-NMR (DMSO-d6, 400 MHz) δ 11.95 (br. s, 1H), 7.47˜7.68 (m, 3H), 7.35 (d, J=8.0 Hz, 1H), 7.11˜7.19 (m, 1H), 6.81 (dd, J=8.0, 10.4 Hz, 1H). MS (M+H)+: 246.

Workup

  1. customAfter the solvent was removed
  2. customthe residue was purified by prep-TLC (DCM:EtOAc=10:1)

Sources & evidence

ORD record
ord-8e7c892558a24affa9fe7259afa67314
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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