2,2'-Bipyridine → HCID 71063089, compound

HRID 535690Notes

Reaction equation

HRID 535690 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-c3865c6f70044b68b987798385051ef7
Source dataset
uspto-grants-2014_10
Patent number
US08859536B2

Reaction notes

Loading…