Potassium Carbonate → HCID 86623947, compound

HRID 886567Notes

Reaction equation

HRID 886567 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.[CH2:37]([O:39][C:40](=[O:49])[CH2:41]C1C=NC=C(Cl)N=1)[CH3:38].C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(#N)C>[CH2:37]([O:39][C:40](=[O:49])[CH2:41][C:15]1[CH:16]=[C:17]2[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])=[CH:10][N:11]([S:27]([C:30]3[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=3)(=[O:29])=[O:28])[C:12]2=[N:13][CH:14]=1)[CH3:38]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 160390673-(2-Methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 52987963HCID 52987963, compound

Product 1

HCID 86623947HCID 86623947, compoundYield 74.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 6342AcetonitrileSolvent

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 (938 mg, 3.02 mmol), (6-Chloro-pyrazin-2-yl)-acetic acid ethyl ester (605 mg, 3.02 mmol), palladium acetate (20.8 mg, 0.093 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (76.3 mg, 0.186 mmol) were combined under nitrogen. Acetonitrile (10 mL) and 1 M potassium carbonate (5.5 mL, 5.5 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 {6-[3-(2-methoxyphenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-yl-acetic acid ethyl ester (1.05 g, 64%). MS: m/z 453 (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-2737753319b04fce84aecda1586568d0
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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