Potassium Carbonate → HCID 86295633, compound

HRID 1752607Notes

Reaction equation

HRID 1752607 reaction equation
C([O-])([O-])=O.[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Cl[C:42]1[C:47](=[O:48])[N:46]([CH3:49])[CH:45]=[C:44]2[C:50](=[O:66])[N:51]([CH2:54][CH2:55][C:56]3[CH:65]=[CH:64][C:63]4[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=4)[N:57]=3)[C:52](=[O:53])[C:43]=12.[NH:67]1[CH2:72][CH2:71][S:70](=[O:74])(=[O:73])[CH2:69][CH2:68]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:49][N:46]1[C:47](=[O:48])[C:42]([N:67]2[CH2:72][CH2:71][S:70](=[O:74])(=[O:73])[CH2:69][CH2:68]2)=[C:43]2[C:52](=[O:53])[N:51]([CH2:54][CH2:55][C:56]3[CH:65]=[CH:64][C:63]4[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=4)[N:57]=3)[C:50](=[O:66])[C:44]2=[CH:45]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 6484228Thiomorpholine 1,1-dioxideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 90421601HCID 90421601, compound

Product 1

HCID 86295633HCID 86295633, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

K2CO3 (1.127 g, 8.16 mmol), Pd2(dba)3 (0.249 g, 0.272 mmol) and dicyclohexyl[2′,4′,6′-tris(1-methylethyl)[1,1′-biphenyl]-2-yl]-phosphine (0.13 g, 0.272 mmol) were subsequently added to a suspension of 7-chloro-5-methyl-2-(2-quinolin-2-yl-ethyl)-5H-pyrrolo[3,4-c]pyridine-1,3,6-trione (1 g, 2.72 mmol, see Example c1)) and thiomorpholine 1,1-dioxide (0.551 g, 4.08 mmol) in toluene (10 ml) and the mixture was stirred for 4 h under reflux. The solvent was removed and the resulting mixture was purified on a silica column (DCM/MeOH=50:1) to afford the title compound (0.8 g, 63% yield).

Workup

  1. temperatureunder reflux
  2. customThe solvent was removed
  3. customthe resulting mixture was purified on a silica column (DCM/MeOH=50:1)

Sources & evidence

ORD record
ord-d819d401290e4693ac22200a69a847b8
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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