Potassium Carbonate → HCID 86711963, compound

HRID 1475272Notes

Reaction equation

HRID 1475272 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[O:9][N:8]=2)[NH:5][N:6]=1.C([O-])([O-])=O.[K+].[K+].[Cl:29][C:30]1[CH:35]=[C:34]([CH2:36]Cl)[CH:33]=[CH:32][N:31]=1>CN(C=O)C.O>[Cl:29][C:30]1[CH:35]=[C:34]([CH2:36][N:6]2[C:2]([CH3:1])=[N:3][C:4]([C:7]3[CH:11]=[C:10]([C:12]4[CH:13]=[CH:14][C:15]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:16][CH:17]=4)[O:9][N:8]=3)=[N:5]2)[CH:33]=[CH:32][N:31]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 111265732-Chloro-4-(chloromethyl)pyridineHCID 178434567HCID 178434567, compound

Product 1

HCID 86711963HCID 86711963, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(5-methyl-2H-1,2,4-triazol-3-yl)-5-(4-(trifluoromethoxy)phenyl)isoxazole (Example 96, Step 4, 400 mg, 1.3 mmol) and K2CO3 (445 mg, 3.3 mmol) in DMF (5 mL) was added 2-chloro-4-(chloromethyl)pyridine (210 mg, 1.3 mmol). The mixture was stirred at RT for 2 h, then diluted with H2O (30 mL) and extracted with EtOAc (2×40 mL). The combined organic layers were washed with H2O (20 mL) and concentrated under reduced pressure to afford the crude product, which was purified by silica gel chromatography (Petroleum ether:EA=1:3) to give the title compound as a light yellow solid (300 mg, 53.3%). MS (ES+) C19H13ClF3N5O2 requires: 435. found: 436 [M+H]+.

Workup

  1. extractionextracted with EtOAc (2×40 mL)
  2. washThe combined organic layers were washed with H2O (20 mL)
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product, which
  5. customwas purified by silica gel chromatography (Petroleum ether:EA=1:3)

Sources & evidence

ORD record
ord-1b59512938d242a19f53ad4c4a0ace11
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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