Potassium Carbonate → HCID 59436060, compound

HRID 1802513Notes

Reaction equation

HRID 1802513 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.[NH2:43][CH2:44][CH:45]([C:47]1[CH:52]=[N:51][CH:50]=[CH:49][N:48]=1)[OH:46].N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C.[Cu]I>[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]([NH:43][CH2:44][CH:45]([OH:46])[C:47]3[CH:52]=[N:51][CH:50]=[CH:49][N:48]=3)[CH:42]=[CH:41][C:5]=2[N:6]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 21928082HCID 21928082, compoundHCID 59435985HCID 59435985, compound

Product 1

HCID 59436060HCID 59436060, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

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 (Example 172, Step 1) (50 mg, 0.07 mmol) and 2-amino-1-pyrazin-2-ylethanol (14.6 mg, 0.11 mmol) in DMSO (1 ml) was added L-proline (2 mg, 0.014 mmol), potassium carbonate (29.7 mg, 0.14 mmol) and CuI (1.3 mg, 7.01 μmol). The solution was heated to 100° C. in a sealed tube for 16 h. After cooling to room temperature, the reaction was diluted with ethyl acetate and washed with water. The organic layer was dried with sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ceb9d0bc27740d9b7eec5c200975991
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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