Potassium Carbonate → HCID 66863597, compound

HRID 1944014Notes

Reaction equation

HRID 1944014 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19]([NH2:21])=[O:20])=[CH:5]2.[Br:22][C:23]1[CH:24]=[CH:25][C:26]2[N:27]([CH:29]=[C:30]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[N:31]=2)[N:28]=1.C(=O)([O-])[O-].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>O1CCOCC1.[Cu](I)I>[Br:22][C:23]1[CH:24]=[CH:25][C:26]2[N:27]([CH:29]=[C:30]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[N:31]=2)[N:28]=1.[CH2:35]([O:34][C:32]([C:30]1[N:31]=[C:26]2[CH:25]=[CH:24][C:23]([NH:21][C:19]([C:6]3[N:7]([CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=4)[C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([F:1])=[CH:10][CH:9]=4)=[O:20])=[N:28][N:27]2[CH:29]=1)=[O:33])[CH3:36]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 668456965-Fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamideHCID 70701127Ethyl 6-bromoimidazo[1,2-b]pyridazine-2-carboxylate

Product 2

HCID 66863597HCID 66863597, compoundYield 5.5%HCID 70701127Ethyl 6-bromoimidazo[1,2-b]pyridazine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Compound 21 was prepared according to a process similar to that described in Example 20, by reacting 0.4 g (1.40 mmol) of 5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide, prepared according to the protocol described in step 1.2, with 0.41 g (1.54 mmol) of ethyl 6-bromoimidazo[1,2-b]pyridazine-2-carboxylate, prepared according to the protocol described in step 21.1, in the presence of 80 mg (0.42 mmol) of copper iodide, 0.38 g (2.79 mmol) of potassium carbonate and 53 mg (0.46 mmol) of trans-1,2-cyclohexanediamine in 10 mL of dioxane. 20 mg of the expected product are thus obtained.

Workup

  1. customprepared
  2. customprepared

Sources & evidence

ORD record
ord-980f62dee8b84486864e3d3e9d696d75
Source dataset
uspto-grants-2013_03
Patent number
US08394820B2

Reaction notes

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