Potassium Carbonate → HCID 57731610, compound

HRID 2234705Notes

Reaction equation

HRID 2234705 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:16]=2)[N:11]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[CH:10]=1.[CH3:37][N:38]([CH3:49])[C:39]([C:41]1[CH:46]=[C:45](Cl)[N:44]=[N:43][C:42]=1[NH2:48])=[O:40].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCCC1.C(#N)C>[CH3:37][N:38]([CH3:49])[C:39]([C:41]1[CH:46]=[C:45]([C:15]2[CH:16]=[C:17]3[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])=[CH:10][N:11]([S:27]([C:30]4[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=4)(=[O:28])=[O:29])[C:12]3=[N:13][CH:14]=2)[N:44]=[N:43][C:42]=1[NH2:48])=[O:40]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 160390673-(2-Methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 57731532HCID 57731532, compound

Product 1

HCID 57731610HCID 57731610, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

3-(2-Methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (138.4 mg, 0.274 mmol), 3-amino-6-chloro-pyridazine-4-carboxylic acid dimethylamide (54.9 mg, 0.274 mmol), palladium acetate (3.0 mg, 0.013 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (11.2 mg, 0.0274 mmol) were combined under nitrogen. Acetonitrile (0.5 mL), tetrahydrofuran (0.5 mL) and 1 M aqueous potassium carbonate (0.822 mL, 0.822 mmol) were added and the vial was flushed with nitrogen, capped and heated at 80° C. for 15 h. The layers were separated. The organics were diluted with ethyl acetate and washed with brine (1×), dried over sodium sulfate and adsorbed onto silica gel. The material was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford 3-amino-6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridazine-4-carboxylic acid dimethylamide. MS: m/z 543 (M+H+).

Workup

  1. customthe vial was flushed with nitrogen
  2. customcapped
  3. customThe layers were separated
  4. additionThe organics were diluted with ethyl acetate
  5. washwashed with brine (1×)
  6. dry with materialdried over sodium sulfate
  7. customThe material was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9cf9b3a03f59490a93f445f05950c228
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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