Morpholine → HCID 59436088, compound

HRID 1802511Notes

Reaction equation

HRID 1802511 reaction equation
Br[C:2]1[CH:42]=[CH:41][C:5]2[N:6]=[C:7]([N:23]([C:32]3[C:37]([Cl:38])=[CH:36][C:35]([F:39])=[CH:34][C:33]=3[Cl:40])[CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:8]3[CH:9]=[CH:10][N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.[NH:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[Cl:38][C:37]1[CH:36]=[C:35]([F:39])[CH:34]=[C:33]([Cl:40])[C:32]=1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:7]1[C:8]2[CH:9]=[CH:10][N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:21])([CH3:22])[CH3:20])[C:12](=[O:14])[C:13]=2[C:4]2[CH:3]=[C:2]([N:43]3[CH2:48][CH2:47][O:46][CH2:45][CH2:44]3)[CH:42]=[CH:41][C:5]=2[N:6]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59435985HCID 59435985, compound

Product 1

HCID 59436088HCID 59436088, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 9-bromo-5((2,6-dichloro-4-fluorophenyl){[2-(trimethylsilyl)ethoxy]methyl}amino)-2-{[2-(trimethylsilyl)ethoxy]methyl}benzo[c]-2,6-naphthyridin-1(2H)-one (58 mg, 0.08 mmol) in dioxane (2 ml) was added morpholine (14.16 mg, 0.16 mmol), xantphos (9.41 mg, 0.02 mmol), cesium carbonate(79 mg, 0.24 mmol) and Pd2(dba)3 (7.44 mg, 8.13 μmol). The solution was degassed by bubbling nitrogen for few minutes and heated to 100° C. in a sealed tube for 16 h. After cooling to room temperature, the reaction mixture was filtered and the filtrate was evaporated under vacuum to afford the title compound.

Workup

  1. customThe solution was degassed
  2. customby bubbling nitrogen for few minutes
  3. temperatureAfter cooling to room temperature
  4. filtrationthe reaction mixture was filtered
  5. customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-b386bf126f2843128195622f856e7aff
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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