Water → HCID 11323995, compound

HRID 746837Notes

Reaction equation

HRID 746837 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:9]2)[N:3]=1.C(B(CC)[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)C.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[CH:11]=[CH:12][N:8]([C:4]2[N:3]=[C:2]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH:7]=[CH:6][CH:5]=2)[CH:9]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 10236225HCID 10236225, compound

Product 1

HCID 11323995HCID 11323995, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-6-(3-pyridin-2-yl-1H-pyrrol-1-yl)pyridine (256 mg, 1.0 mmol), diethyl-(3-pyridyl)borane (162 mg, 1.1 mmol), bis(triphenylphosphine)palladium dichloride (35 mg, 0.05 mmol), and potassium carbonate (345 mg, 2.5 mmol) were combined in 3 mL of 1:1 DME:H2O and heated via microwave irradiation for 5 min at 160° C. The reaction was diluted with 50 mL EtOAc and partitioned with H2O (50 mL). The EtOAc layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by SiO2 chromatography, eluting with a 20-75% EtOAc in hexanes gradient to afford 6-(3-pyridin-2-yl-1H-pyrrol-1-yl)-2,3′-bipyridine as a tan solid that was dissolved in ether and precipitated as an HCl salt by slow addition of 6 equivalents of 1N HCl in ether. H-NMR (CD3OD, 500 MHz) δ 9.82 (s, 1H), 9.48 (d, 1H), 9.14 (dd, 1H), 8.95 (d, 1H), 8.62 (d, 1H), 8.52 (dd, 1H), 8.44 (d, 1H), 8.28 (dd, 1H), 8.17-8.25 (m, 2H), 8.04 (m, 1H), 7.95 (d, 1H), 7.78 (dd, 1H), 7.15 (m, 1H). MS (ESI) 299.44 (M+H+).

Workup

  1. custompartitioned with H2O (50 mL)
  2. dry with materialThe EtOAc layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by SiO2 chromatography
  6. washeluting with a 20-75% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-d0bdcdf385e746d58aab3c1f903cfdf6
Source dataset
uspto-grants-2008_07
Patent number
US07393959B2

Reaction notes

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