2,2'-Bipyridine → 4-Bromo-1-cyclopropylpyridin-2(1H)-one

HRID 919304Notes

Reaction equation

HRID 919304 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([OH:8])[CH:3]=1.[CH:9]1(B(O)O)[CH2:11][CH2:10]1.C1C=CN=C(C2C=CC=CN=2)C=1>CC([O-])=O.CC([O-])=O.[Cu+2]>[Br:1][C:2]1[CH:7]=[CH:6][N:5]([CH:9]2[CH2:11][CH2:10]2)[C:4](=[O:8])[CH:3]=1

Participants

5

Reactant 3

HCID 14742,2'-BipyridineHCID 2760897Cyclopropylboronic acidHCID 178515446HCID 178515446, compound

Product 1

HCID 596356474-Bromo-1-cyclopropylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Conditions

Temperature
70 °C

Procedure

A mixture of 4-bromopyridin-2-ol (100 mg, 0.58 mmol), cyclopropylboronic acid (100 mg, 1.3 mmol), Cu(OAc)2 (245 mg, 1.2 mmol), and bipyridine (100 mg, 0.64 mmol) in Cl(CH2)2C1 (5.0 mL) was stirred for 24 h at 70° C. The crude mixture was filtered. The filtrate was collected and concentrated to afford the crude product, which was purified by silica gel column chromatography on silica gel with PE/EA (5:1) to afford tittle compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.20 (d, 1 H), 6.79 (d, 1 H), 6.31 (dd, 1 H), 3.34-3.23 (m, 1 H), 1.14 (d, 2 H), 0.86 (d, 2 H).

Workup

  1. filtrationThe crude mixture was filtered
  2. customThe filtrate was collected
  3. concentrationconcentrated
  4. customto afford the crude product, which
  5. customwas purified by silica gel column chromatography on silica gel with PE/EA (5:1)
  6. customto afford tittle compound as a white solid

Sources & evidence

ORD record
ord-c012f4e3f2e845ff8154daf4a3a16bbc
Source dataset
uspto-grants-2016_03
Patent number
US09273033B2

Reaction notes

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