2,2'-Bipyridine → HCID 71063089, compound

HRID 921007Notes

Reaction equation

HRID 921007 reaction equation
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.[Br:7][C:8]1[CH:9]=[C:10]2[CH:16]=[CH:15][NH:14][C:11]2=[N:12][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].N1C=CC=CC=1C1C=CC=CN=1>ClC(Cl)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:7][C:8]1[CH:9]=[C:10]2[CH:16]=[CH:15][N:14]([CH:1]3[CH2:3][CH2:2]3)[C:11]2=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 14742,2'-BipyridineHCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 71063089HCID 71063089, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
110 °C

Procedure

Cyclopropylboronic acid (0.872 g, 10.15 mmol) was added to a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (1 g, 5.08 mmol), Na2CO3 (1.076 g, 10.15 mmol), copper(II)acetate (0.922 g, 5.08 mmol) and 2,2′-bipyridine (0.793 g, 5.08 mmol) in dichloroethane (20 mL), and the mixture was stirred at 110° C. for 8 h. The reaction mixture was concentrated, and then diluted with ethyl acetate and water. Organic layer was separated, washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in reduced pressure and purified by flash chromatography using 10% ethyl acetate in pet ether to afford title compound (0.38 g, 31.3%) as oil. 1H NMR (300 MHz, CDCl3): δ 8.38 (d, J=2.1 Hz, 1H), 7.99 (d, J=2.1 Hz, 1H), 7.20 (d, J=3.3 Hz, 1H), 6.34 (d, J=3.6 Hz, 1H), 3.5 (m, 1H), 1.15 (m, 2H), 1.03 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate and water
  3. customOrganic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in reduced pressure
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-4b7a9f999dd743968b40519c08de3d69
Source dataset
uspto-grants-2016_03
Patent number
US09273069B2

Reaction notes

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