Sodium Carbonate → HCID 58917760, compound

HRID 639711Notes

Reaction equation

HRID 639711 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[F:7][C:8]1[C:13](I)=[CH:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][N:9]=1.[C:21]([N:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]1B(O)O)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>O.C1(C)C=CC=CC=1.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:7][C:8]1[C:13]([C:29]2[N:28]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:36]3[C:31]([CH:30]=2)=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][N:9]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 463148322-Fluoro-3-iodo-5-phenylpyridine

Product 1

HCID 58917760HCID 58917760, compoundYield 76.3%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

Na2CO3 (279 mg, 2.63 mmol, 6.9 Eq.) in water (2 mL) was added to a mixture of 2-fluoro-3-iodo-5-phenyl-pyridine (114 mg, 0.38 mmol, 1.0 Eq.), Pd(PPh3)4 (44 mg, 0.04 mmol, 10 mol %) and 1-boc-indole-2-boronic acid (116 mg, 0.57 mmol, 1.5 Eq.) in toluene (5 mL) and EtOH (1 mL). The reaction was heated at reflux under nitrogen overnight. After cooling to ambient temperature the reaction mixture was diluted with water (10 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by column chromatography on SiO2, eluting with 10% Et2O/petroleum ether to give the desired compound as a white foam (113 mg, 0.29 mmol, 76%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux under nitrogen overnight
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by column chromatography on SiO2
  8. washeluting with 10% Et2O/petroleum ether

Sources & evidence

ORD record
ord-03aab598fc0d40ac9bb7b25ee11a46c1
Source dataset
uspto-grants-2010_04
Patent number
US07691885B2

Reaction notes

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