Potassium Carbonate → HCID 66863244, compound

HRID 1944008Notes

Reaction equation

HRID 1944008 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[C:7]([C:20]([NH2:22])=[O:21])=[CH:6]2.[NH2:25][C:26]1[CH:31]=[C:30](Br)[CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>[Cu](I)I.O.O1CCOCC1>[NH2:25][C:26]1[CH:31]=[C:30]([NH:22][C:20]([C:7]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[C:9]3[C:5]([CH:6]=2)=[CH:4][C:3]([C:2]([F:1])([F:23])[F:24])=[CH:11][CH:10]=3)=[O:21])[CH:29]=[CH:28][N:27]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 6932822-Amino-4-bromopyridineHCID 66863596HCID 66863596, compound

Product 1

HCID 66863244HCID 66863244, compoundYield 73.6%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
170 °C

Procedure

0.056 g (0.30 mmol) of copper iodide, 0.2 g (0.59 mmol) of 5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide, prepared according to the protocol described in step 17.1, 0.12 g (0.71 mmol) of 2-amino-4-bromopyridine, 0.33 g (2.38 mmol) of potassium carbonate and 4 mL of anhydrous dioxane are placed in a 10 mL pressure tube specific for microwave reactors. The suspension is degassed for a few minutes and 0.04 mL (0.3 mmol) of trans-1,2-cyclohexanediamine is then added. The tube is then sealed and heated in the microwave reactor at 170° C. for 45 minutes. After this time, the suspension cooled to room temperature is poured into 30 mL of water and then extracted with 2×40 mL of dichloromethane. The combined organic phases are dried over magnesium sulfate and concentrated under reduced pressure. The crude reaction product is then purified by chromatography on a column of silica gel, eluting with a mixture of dichloromethane and methanol. 0.186 g of the expected product is thus obtained.

Workup

  1. customare placed in a 10 mL pressure tube
  2. customThe suspension is degassed for a few minutes
  3. customThe tube is then sealed
  4. temperatureAfter this time, the suspension cooled to room temperature
  5. extractionextracted with 2×40 mL of dichloromethane
  6. dry with materialThe combined organic phases are dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude reaction product
  9. customis then purified by chromatography on a column of silica gel
  10. washeluting with a mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-3ae1f84a1c2d430e920258d830cd7e1c
Source dataset
uspto-grants-2013_03
Patent number
US08394820B2

Reaction notes

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